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Chemistry
Heterocyclic Building Blocks
Quinuclidines
(R)-Quinuclidin-3-amine hydrochloride
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks Asymmetric Synthesis
Quinuclidines
Amines Chiral Building Blocks Aliphatic Heterocycles

[ CAS No. 137661-31-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 137661-31-5
Chemical Structure| 137661-31-5
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Quality Control of [ 137661-31-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 137661-31-5 ]

CAS No. :137661-31-5 MDL No. :MFCD16036190
Formula : C7H15ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 162.66 Pubchem ID :-
Synonyms :

Safety of [ 137661-31-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 137661-31-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 137661-31-5 ]

[ 137661-31-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 137661-31-5 ]
  • [ 19075-58-2 ]
  • N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1-benzothiophene-2-carboxamide hydrochloride [ No CAS ]
Reference： [1]Patent: WO2004/13136,2004,A1 .Location in patent: Page/Page column 36; 41
  • 2
  • [ 19075-59-3 ]
  • [ 137661-31-5 ]
  • N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride [ No CAS ]
Reference： [1]Patent: WO2004/13136,2004,A1 .Location in patent: Page/Page column 36; 41
  • 3
  • [ 478148-62-8 ]
  • [ 137661-31-5 ]
  • [ 478149-53-0 ]
YieldReaction ConditionsOperation in experiment
66% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In chloroform; at 20℃; for 16.0h; First Step Synthesis of N-(1-Azabicyclo[2.2.2]oct-3(R)-yl)furo[2,3-c]pyridine-5-carboxamide To a solution (10 mL) of <strong>[478148-62-8]furo[2,3-c]pyridine-5-carboxylic acid</strong> (0.16 g, 1.0 mmol) in chloroform, o-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (0.57 g, 1.5 mmol), diisopropylethylamine (0.70 mL, 4.0 mmol), and (R)-quinuclidine-3-amine hydrochloride (0.20 g, 1.0 mmol) were added, and the resulting mixture was stirred at room temperature. Sixteen hours later, distilled water was added thereto, and the resultant was then extracted with chloroform. The organic layer was washed with brine, then dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (amine silica gel DM1020, Fuji Silysia Chemical Ltd., chloroform alone to chloroform/methanol=98/2) to obtain the title compound (0.18 mg; 66%) as a colorless liquid. 1H-NMR (400 MHz, CDCl3) delta: 1.40-1.55 (1H, m), 1.65-1.74 (2H, m), 1.80-1.90 (1H, m), 2.02-2.06 (1H, m), 2.63-2.70 (1H, m), 2.75-3.00 (4H, m), 3.39-3.46 (1H, m), 4.12-4.20 (1H, m), 6.89-6.92 (1H, m), 7.80 (1H, d, J=2.0 Hz) 8.25-8.35 (1H, m), 8.46-8.49 (1H, m), 8.75-8.78 (1H, m).MS (ESI) [M+H]+272
Reference： [1]Patent: US2014/128606,2014,A1 .Location in patent: Paragraph 0190; 0191; 0192; 0193; 0194; 0195
  • 4
  • [ 478148-62-8 ]
  • [ 137661-31-5 ]
  • PHA-543,613 [ No CAS ]
Reference： [1]Patent: US2014/128606,2014,A1
  • 5
  • [ 137661-31-5 ]
  • [ 4442-54-0 ]
  • PHA-568487 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In chloroform; at 20℃; for 16h; First Step Synthesis of N-(1-Azabicyclo[2.2.2]oct-3(R)-yl)-2,3-dihydro-1,4-benzodioxin-6-carboxamide To a solution (10 mL) of <strong>[4442-54-0]2,3-dihydro benzo[b][1,4]dioxin-6-carboxylic acid</strong> (0.18 g, 1.0 mmol) in chloroform, o-(benzotriazol-1-yl)-N,N, N',N'-tetramethyluronium hexafluorophosphate (0.57 g, 1.5 mmol), diisopropylethylamine (0.70 mL, 4.0 mmol), and (R)-quinuclidine-3-amine hydrochloride (0.20 g, 1.0 mmol) were added, and the resulting mixture was stirred at room temperature. Sixteen hours later, distilled water was added thereto, and the resultant was then extracted with chloroform. The organic layer was washed with brine, then dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (amine silica gel DM1020, Fuji Silysia Chemical Ltd., chloroform alone to chloroform/methanol=98/2) to obtain the title compound (0.22 mg; 76percent) as a colorless liquid. 1H-NMR (400 MHz, CDCl3)delta: 1.44-1.55 (1H, m), 1.65-1.76 (3H, m), 1.98-2.03 (1H, m), 2.51-2.58 (1H, m), 2.75-2.90 (4H, m), 3.37-3.46 (1H, m), 4.05-4.14 (1H, m), 4.25-4.35 (4H, m), 6.08-6.18 (1H, m), 6.86-6.90 (1H, m), 7.24-7.31 (2H, m).MS (ESI) [M+H]+289
Reference： [1]Patent: US2014/128606,2014,A1 .Location in patent: Paragraph 0202; 0203; 0204; 0205; 0206; 0207
  • 6
  • [ 137661-31-5 ]
  • [ 90407-16-2 ]
  • EVP-6124 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In chloroform; at 20℃; for 16h; Second Step Synthesis of (R)-7-Chloro-N-(quinuclidine-3-yl)benzo[b]thiophene-2-carboxamide To a solution (10 mL) of <strong>[90407-16-2]7-chloro-1-benzothiophene-2-carboxylic acid</strong> (210 mg, 1.0 mmol) in chloroform, o-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (570 mg, 1.5 mmol) and diisopropylethylamine (0.70 mL, 4.0 mmol) were added. Thereafter, (R)-quinuclidine-3-amine hydrochloride (200 mg, 1.0 mmol) was added thereto, and the resulting mixture was stirred at room temperature. Sixteen hours later, distilled water and 1.0 N aqueous sodium hydroxide solution were added thereto, and the resultant was extracted with chloroform. The organic layer was washed with brine, then dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (amine silica gel DM1020, Fuji Silysia Chemical Ltd., chloroform alone to chloroform/methanol=90/10) to obtain the title compound (170 mg; 53%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) delta: 1.22-1.38 (1H, m), 1.53-1.62 (2H, m), 1.75-1.82 (2H, m), 2.63-2.73 (4H, m), 2.84-2.94 (1H, m), 3.07-3.18 (1H, m), 3.90-4.00 (1H, m), 7.49 (1H, dd, J=7.6, 8.0 Hz), 7.59 (1H, d, J=7.6 Hz), 7.96 (1H, d, J=8.0 Hz), 8.31 (1H, s), 8.62-8.66 (1H, m).MS (ESI) [M+H]+321
Reference： [1]Patent: US2014/128606,2014,A1 .Location in patent: Paragraph 0084; 0085; 0086; 0087; 0088; 0089

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