Triethylamine → HCID 86751296, compound

HRID 1379194Notes

Reaction equation

HRID 1379194 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][NH:12][CH2:11][CH2:10][N:9]1[C:14](=[O:29])[C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[ClH:37].[Cl:38][CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1>CN(C)C=O>[ClH:38].[ClH:37].[CH2:1]([C@@H:8]1[CH2:13][N:12]([CH2:39][C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)[CH2:11][CH2:10][N:9]1[C:14](=[O:29])[C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 233943-(Chloromethyl)pyridine hydrochloride2×HCID 54243495HCID 54243495, compound

Product 1

HCID 86751296HCID 86751296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled mixture of (2R)-2-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]piperazine (0.3 g) and triethylamine (0.39 ml) in dimethylformamide (8 ml) was added 3-(chloromethyl)pyridine hydrochloride (0.12 g). The reaction mixture was stirred at the same temperature for 30 minutes and then at room temperature for 2 hours. Additional triethylamine (0.39 ml) and 3-(chloromethyl)pyridine hydrochloride (0.12 g) were added and the resulting mixture was stirred overnight. The reaction mixture was filtered and the filtrate was concentrated and subjected to a chromatography on a silica gel eluting with a mixture of toluene and ethyl acetate (5:1). The eluent was treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-2-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(pyridin-3-yl-methyl)piperazine dihydrochloride.

Workup

  1. waitat room temperature for 2 hours
  2. stirringthe resulting mixture was stirred overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. additionsubjected to a chromatography on a silica gel eluting with a mixture of toluene and ethyl acetate (5:1)
  6. additionThe eluent was treated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-d2cb8c8b77db40319c9adbeb487d7774
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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