Triethylamine → HCID 131723772, compound

HRID 1060197Notes

Reaction equation

HRID 1060197 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].[Cl:18][C:19]1[CH:20]=[C:21]([CH2:26][C@H:27]2[CH2:32][C@H:31]([N:33]3[CH2:38][CH2:37][N:36]([CH2:39][C:40]([NH:42][C:43]4[C:48]([CH3:49])=[CH:47][CH:46]=[CH:45][C:44]=4[CH3:50])=[O:41])[CH2:35][CH2:34]3)[CH2:30][CH2:29][NH:28]2)[CH:22]=[CH:23][C:24]=1[Cl:25].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([N:28]1[CH2:29][CH2:30][C@@H:31]([N:33]2[CH2:34][CH2:35][N:36]([CH2:39][C:40]([NH:42][C:43]3[C:48]([CH3:49])=[CH:47][CH:46]=[CH:45][C:44]=3[CH3:50])=[O:41])[CH2:37][CH2:38]2)[CH2:32][C@@H:27]1[CH2:26][C:21]1[CH:22]=[CH:23][C:24]([Cl:25])=[C:19]([Cl:18])[CH:20]=1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 86619155HCID 86619155, compound

Product 1

HCID 131723772HCID 131723772, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5 di(trifluormethyl)benzoyl chloride (0.0011 mol) was added to a mixture of (±)-trans-4-[2-[(3,4-dichlorophenyl)methyl]-4-piperidinyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide (0.001 mol) in DCM (20ml). The mixture was stirred for 5 minutes. Triethylamine (2ml) was added. The mixture was stirred at RT for 3 hours, washed with a diluted NaOH solution and with water, and then dried. The solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 96/4). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 0.32 g (44%) of (±)-trans-4-[1-[3,5-bis(trifluoromethyl)benzoyl]-2-[(3,4-dichlorophenyl)methyl]-4-piperidinyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide (compound 139).

Workup

  1. stirringThe mixture was stirred at RT for 3 hours
  2. washwashed with a diluted NaOH solution and with water
  3. customdried
  4. customThe solvent was evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 96/4)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from CH3CN
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-36b34a3bd0084ccb94a0293610e190d4
Source dataset
uspto-grants-2003_02
Patent number
US06521621B1

Reaction notes

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