3,5-Bis(trifluoromethyl)phenyl isocyanate → HCID 86619161, compound

HRID 1060199Notes

Reaction equation

HRID 1060199 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([N:13]=[C:14]=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[NH:26][C:27](=[O:48])[CH2:28][N:29]1[CH2:34][CH2:33][N:32]([C@@H:35]2[CH2:40][CH2:39][NH:38][C@@H:37]([CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:36]2)[CH2:31][CH2:30]1>C(Cl)Cl>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:38]2[CH2:39][CH2:40][C@@H:35]([N:32]3[CH2:33][CH2:34][N:29]([CH2:28][C:27]([NH:26][C:20]4[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:19]=4[CH3:18])=[O:48])[CH2:30][CH2:31]3)[CH2:36][C@@H:37]2[CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

4

Reactant 2

HCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 86619162HCID 86619162, compound

Product 1

HCID 86619161HCID 86619161, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,5-di(trifluoromethyl)-1-isocyanatobenzene (0.0025 mol) in DCM (10 ml) was added to a mixture of (±)-trans-N-(2,6-dimethylphenyl)-4-[2-(phenylmethyl)-4-piperidinyl]-1-piperazineacetamide (0.0025 mol) in DCM (15 ml). The mixture was stirred at RT overnight. The precipitate was filtered off and dried, yielding 0.66 g (40%) of (±)-trans-4-[1-[[[3,5-bis(trifluoromethyl)phenyl]amino]carbonyl]-2-(phenylmethyl)-4-piperidinyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide (compound 143).

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-c1864c76323040d38988840f5b5a1b91
Source dataset
uspto-grants-2003_02
Patent number
US06521621B1

Reaction notes

Loading…