Methylamine → HCID 58189011, compound

HRID 1423142Notes

Reaction equation

HRID 1423142 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:36])[CH2:29][CH2:30][C:31]([O:33]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:37][NH2:38].[C-]#N.[Na+]>CCO>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:36])[CH2:29][CH2:30][C:31]([NH:38][CH3:37])=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8929Sodium CyanideHCID 86652000HCID 86652000, compound

Product 1

HCID 58189011HCID 58189011, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (S)-ethyl 4-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-4-oxobutanoate (124 mg, 0.25 mmol) in a ˜33% methylamine solution in EtOH (5 mL) was treated with catalytic amount of sodium cyanide and allowed to heat at 50° C. for 3 days. The reaction mixture was then evaporated, washed with water and air dried to afford the title compound as a colorless foam (100 mg, 83%). LC/MS (Method B) 3.23 min, [M+1]+ 480.

Workup

  1. customThe reaction mixture was then evaporated
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-64a4d1eacfb04c2e925a6d7cf39924a6
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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