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Chemical Structure| 1430230-59-3 Chemical Structure| 1430230-59-3

Structure of 1430230-59-3

Chemical Structure| 1430230-59-3

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Product Details of [ 1430230-59-3 ]

CAS No. :1430230-59-3
Formula : C6H14ClNO
M.W : 151.63
SMILES Code : OC1(C)C(N)CCC1.[H]Cl
MDL No. :MFCD32695522

Safety of [ 1430230-59-3 ]

Application In Synthesis of [ 1430230-59-3 ]

* 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 [ 1430230-59-3 ]

[ 1430230-59-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 796600-15-2 ]
  • [ 1430230-59-3 ]
  • 2-chloro-4-[[2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile [ No CAS ]
  • 2-chloro-4-[[2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
12%; 20% With lithium carbonate; In water; dimethyl sulfoxide; at 130℃; for 28h;Inert atmosphere; Sealed tube; Alternate procedure (Example 2A & 2B)Example 2Acz5-2-Chloro-4-[[2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrile2-Chloro-4-fluoro-3-methyl-benzonitrile (12.4 g, 73.2 mmol) is added to a solution of freshly prepared racemic 2-amino-l-methyl-cyclopentanol, hydrochloride (20.4 g) in DMSO (145 mL) in a pressure reactor vessel. Lithium carbonate (15.5 g, 209 mmol) and water (14.5 mL) are added. The mixture is stirred and degassed with nitrogen for 10 min. The reactor is sealed and the reaction stirred at 130 C for 28 h. The mixture is cooled to room temperature and diluted with water (1 L) and MTBE (150 mL). The mixture is stirred for 10 min at room temperature and filtered through a pad of diatomaceous earth. The organic layer is separated and the aqueous layer extracted with MTBE (2 x 100 mL). The organic portions are combined, dried over sodium sulfate, filtered, and evaporated to afford crude material. The material is purified using silica gel chromatography eluting first with 100% methylene chloride to obtain the cw-2-chloro-4-[[2-hydroxy-2-methyl-cyclopentyl]amino]-3- methyl-benzonitrile compound (5.6 g, 20%). 1H NMR (300 MHz, DMSO-d6) delta 7.47 (d, J= 8.6 Hz, 1H), 6.63 (d, J= 8.8 Hz, 1H), 5.26-5.30 (m, 1H), 4.93 (s, 1H), 3.46-3.50 (m, 1H), 2.14 (s, 3H), 2.12-2.13 (m, 1H), 1.71-1.73 (m, 5H), 1.16 (s, 3H). LC-ES/MS m/z 265.2 (M+l).After isolation of the cis isomer, elution is continued using a mixture of methylene chloride/EtOAc (9/1) to afford (3.6 g, 12%) of the trarcs-2-chloro-4-[[2-hydroxy-2-methyl- cyclopentyl]amino]-3-methyl-benzonitrile. 1H NMR (300 MHz, DMSO-d6) delta 7.48 (d, 1H), 6.90 (d, 1H), 5.51 (d, 1H), 4.66 (s, 1H), 3.65-3.74 (m, 1H), 2.21 (s, 1H), 2.01-2.13 (m, 1H), 1.50-1.78 (m, 5H), 1.07 (s, 3H). LC-ES/MS m/z 265.2 (M+l).
 

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