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[ CAS No. 67123-97-1 ]

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2D
Chemical Structure| 67123-97-1
Chemical Structure| 67123-97-1
Structure of 67123-97-1 *Storage: {[proInfo.prStorage]}

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Product Details of [ 67123-97-1 ]

CAS No. :67123-97-1MDL No. :MFCD00191496
Formula : C10H11NO2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :177.20Pubchem ID :95489
Synonyms :

Computed Properties of [ 67123-97-1 ]

TPSA : 49.3 H-Bond Acceptor Count : 3
XLogP3 : -1.3 H-Bond Donor Count : 2
SP3 : 0.30 Rotatable Bond Count : 1

Safety of [ 67123-97-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67123-97-1 ]

  • Upstream synthesis route of [ 67123-97-1 ]
  • Downstream synthetic route of [ 67123-97-1 ]

[ 67123-97-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 67123-97-1 ]
  • [ 26947-41-1 ]
Reference: [1] Organic Preparations and Procedures International, 1994, vol. 26, # 4, p. 429 - 438
  • 2
  • [ 67123-97-1 ]
  • [ 50458-77-0 ]
Reference: [1] Organic Preparations and Procedures International, 1994, vol. 26, # 4, p. 429 - 438
  • 3
  • [ 67123-97-1 ]
  • [ 50458-79-2 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1986, vol. 36, # 1, p. 10 - 13
[2] Patent: US5089495, 1992, A,
[3] Patent: EP381375, 1990, A1,
  • 4
  • [ 67123-97-1 ]
  • [ 27104-73-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 17, p. 3978 - 3981
[2] Organic Preparations and Procedures International, 1994, vol. 26, # 4, p. 429 - 438
[3] Journal of Medicinal Chemistry, 1982, vol. 25, # 9, p. 1081 - 1091
[4] Patent: CN107137355, 2017, A,
  • 5
  • [ 67123-97-1 ]
  • [ 54329-54-3 ]
YieldReaction ConditionsOperation in experiment
53% With hydrogenchloride; formaldehyd In formic acid; water PREPARATION 3
2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
A solution of 0.364 g (2.07 mmol) of 3-carboxy-1,2,3,4-tetrahydroisoquinoline in 25 mL of formic acid was combined with 2.5 mL of 37percent formaldehyde.
The resulting mixture was allowed to reflux for approximately 17 hours.
After cooling, the mixture was contentrated under reduced pressure to provide a gum.
This gum was dissolved in 3.0 mL of water, adjusted to a pH 2 using hydrochloric acid and then purified using ion-exchange chromatography (Dowex 50x-8, 100 meshcation) to provide 0.21 g of a yellow powder.
Yield: 53percent
1 H NMR (DMSO-d6): δ2.56 (S, 3H), 3.01 (m, 2H), 3.48 (t, 1H), 3.9 (dd, 2H) 7.05 (m, 1H), 7.13 (m, 3H).
MS (FD): m/e 192 (M+2).
Reference: [1] Patent: US5491166, 1996, A,
  • 6
  • [ 50-00-0 ]
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  • [ 54329-54-3 ]
Reference: [1] Patent: WO2010/83384, 2010, A2, . Location in patent: Page/Page column 64
  • 7
  • [ 67123-97-1 ]
  • [ 18881-17-9 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide; boron trifluoride In tetrahydrofuran; methanol Step 1
Synthesis of S-(1,2,3,4-Tetrahydro-Isoquinoline-3-yl)-Methanol STR38
Borane-methyl sulfide complex (31.0 mmol) was added to the gently refluxing solution of S-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (5.0 g, 28.22 mmol) and boron trifluoride ethorate (28.22 mmol) in THF (100 ML) under nitrogen.
The solution was then refluxed overnight.
The reaction mixture was cooled to 0° C. and quenched by slow addition of methanol (5 ML).
the solvent was evaporated and the residue was dissolved in aqueous solution of sodium hydroxide (6 M) and reflux for 2 hr. the mixture was filtered through a cerite pad.
The filtrate was extracted with chloroform, washed with brine, dried over MgSO4 and evaporated.
The crude product was recrystallized from CHCl3 to give the desired product as crystals (4.0 g, 87percent).
1 H NMR (CDCl3) δ: 7.10 (4 H, m), 4.06 (2H, s), 3.77 (1H, dd, J=10.95 Hz, J=3.64 Hz), 3.52 (1H, dd, J=10.95 Hz, J=7.80 Hz), 3.08 (1H, m), 2.70 (1H, dd, J=16.27 Hz, J=4.26 Hz), 2.59 (1H, dd, J=16.27 Hz, J=10.85 Hz).
13 C NMR (CDCl3) δ: 128.43, 125.34, 125.14, 124.98, 64.81, 54.18, 46.97, 30.05.
Reference: [1] Patent: US6034097, 2000, A,
  • 8
  • [ 67123-97-1 ]
  • [ 24424-99-5 ]
  • [ 151838-62-9 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 40, p. 7205 - 7208
[2] Medicinal Chemistry, 2010, vol. 6, # 6, p. 355 - 373
[3] Patent: US2008/255188, 2008, A1, . Location in patent: Page/Page column 10
  • 9
  • [ 67123-97-1 ]
  • [ 151838-62-9 ]
Reference: [1] Patent: US6083903, 2000, A,
[2] Patent: US5780454, 1998, A,
  • 10
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  • [ 58632-95-4 ]
  • [ 151838-62-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 265 - 286
  • 11
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  • [ 103733-65-9 ]
Reference: [1] Synthesis, 1992, # 11, p. 1157 - 1160
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