Methyl iodide → Methyl 2-methyl-2-phenyl-5-{4-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-N-methyl-amino]-piperidin-1-yl}-pentanecarboxylate

HRID 1167109Notes

Reaction equation

HRID 1167109 reaction equation
[H-].[Na+].[CH3:3][C:4]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]([C:22]2[C:23]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[CH2:15][CH2:14]1)[CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH3:44]I>CN(C)C=O>[CH3:3][C:4]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([N:19]([C:20]([C:22]2[C:23]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:30][CH:29]=3)=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[CH3:44])[CH2:17][CH2:18]1)[CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22995529Methyl 2-methyl-2-phenyl-5-{4-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-piperidin-1-yl}-pentanecarboxylate

Product 1

HCID 22995623Methyl 2-methyl-2-phenyl-5-{4-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-N-methyl-amino]-piperidin-1-yl}-pentanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.095 g (0.803 mmol) of sodium hydride (55 to 65% in oil) are added to a solution of 0.4 g (0.724 mmol) of methyl 2-methyl-2-phenyl-5-{4-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-piperidin-1-yl}-pentanecarboxylate in 5 ml of dimethylformamide at ambient temperature and stirred for one hour. Then 0.05 ml (0.803 mmol) of methyl iodide are added and the mixture is stirred for 14 hours. The reaction solution is poured onto water, extracted with ethyl acetate, and the organic phase is dried over sodium sulphate. The product is purified by column chromatography on silica gel (eluant: dichloromethane/methanol=5:1).

Workup

  1. stirringthe mixture is stirred for 14 hours
  2. additionThe reaction solution is poured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. customThe product is purified by column chromatography on silica gel (eluant: dichloromethane/methanol=5:1)

Sources & evidence

ORD record
ord-d437bc1c3c4347738e67317dc95dccbc
Source dataset
uspto-grants-2003_09
Patent number
US06617325B1

Reaction notes

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