Triethylamine → HCID 86751309, compound

HRID 1379203Notes

Reaction equation

HRID 1379203 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)[C@H:8]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([CH3:36])[CH:30]=2)[CH2:7]1.C(N(CC)CC)C.[CH3:44][S:45]([Cl:48])(=[O:47])=[O:46]>ClCCl>[ClH:48].[F:22][C:19]([F:21])([F:20])[C:17]1[CH:18]=[C:13]([CH:14]=[C:15]([C:23]([F:24])([F:26])[F:25])[CH:16]=1)[C:12]([N:9]1[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][NH:3][S:45]([CH3:44])(=[O:47])=[O:46])[CH2:7][C@H:8]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([CH3:36])[CH:30]=1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86751310HCID 86751310, compound

Product 1

HCID 86751309HCID 86751309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (2R)-4-(2-aminoethyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine dihydrochloride (110 mg), triethylamine (0.2 ml) in dichloromethane (10 ml) was added methanesulfonyl chloride (0.1 ml) at 0° C. After stirring for 1 hour, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed successively with aqueous saturated sodium bicarbonate solution and brine, and dried. After evaporation of the solvent in vacuo, the residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (40:1) and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[2-(mesylamino)ethyl]piperazine hydrochloride (50 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with aqueous saturated sodium bicarbonate solution and brine
  3. customdried
  4. customAfter evaporation of the solvent in vacuo
  5. customthe residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (40:1)
  6. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-13bffc5d224c4bf08efec98e84046c60
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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