Ammonia methanol → HCID 86751293, compound

HRID 1379192Notes

Reaction equation

HRID 1379192 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][N:12]([CH2:14][C:15](OC)=[O:16])[CH2:11][CH2:10][N:9]1[C:19](=[O:34])[C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[NH3:37]>>[CH2:1]([C@@H:8]1[CH2:13][N:12]([CH2:14][C:15](=[O:16])[NH2:37])[CH2:11][CH2:10][N:9]1[C:19](=[O:34])[C:20]1[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[C:22]([C:30]([F:32])([F:31])[F:33])[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 86751294HCID 86751294, compound

Product 1

HCID 86751293HCID 86751293, compound

Procedure

(2R)-2-Benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(methoxycarbonylmethyl)piperazine (0.2 g) was treated with 20% ammonia methanol solution (5 ml), and the resulting mixture was left overnight in a refrigerator. The reaction mixture was concentrated under reduced pressure and the residue was purified on a silica gel column (7 g) eluting with a mixture of dichloromethane and methanol (10:1) to give (2R)-2-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(carbamoylmethyl)piperazine. This compound was treated with 4N hydrogen chloride in ethyl acetate solution to give the corresponding hydrochloride (0.18 g) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified on a silica gel column (7 g)
  3. washeluting with a mixture of dichloromethane and methanol (10:1)

Sources & evidence

ORD record
ord-f100d466505a44bbb1fcb8e617d4aa40
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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