Potassium Carbonate → HCID 69819648, compound

HRID 1006355Notes

Reaction equation

HRID 1006355 reaction equation
[ClH:1].Cl.[CH:3]([CH:16]1[NH:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:32][C:33]([NH2:35])=[O:34].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:1].[ClH:1].[CH:3]([CH:16]1[CH2:17][N:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH2:19][CH2:20][N:21]1[CH2:32][C:33](=[O:34])[NH2:35])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 22674563HCID 22674563, compound

Product 1

HCID 69819648HCID 69819648, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-benzhydryl-1-(2-methoxybenzyl)piperazine dihydrochloride (44.5 mg), bromoacetamide (20.7 mg) and potassium carbonate (41.5 mg) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 18 hours. The mixture was partitioned between ethyl acetate and 2N sodium hydroxide. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (70:1). The fractions containing the objective compound were collected, evaporated under reduced pressure and treated with 4N hydrogen chloride in ethyl acetate solution to give 2-benzhydryl-1-carbamoylmethyl-4-(2-methoxybenzyl) piperazine dihydrochloride (21.6 mg) as a colorless powder.

Workup

  1. customThe mixture was partitioned between ethyl acetate and 2N sodium hydroxide
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (70:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure
  10. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-5ba24010e6fe453b9cb35d1d0bf88e29
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

Loading…