Sodium Carbonate → trans-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-4-[[3-(trifluoromethyl)benzoyl]amino]-1-piperidinebutanamide

HRID 981308Notes

Reaction equation

HRID 981308 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([CH:8]([CH3:28])[CH2:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:4][C@H:3]1[OH:29].[F:30][C:31]([F:42])([F:41])[C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36].C(=O)([O-])[O-].[Na+].[Na+]>O.ClC(Cl)Cl.C(N(CC)CC)C>[OH:29][C@H:3]1[C@H:2]([NH:1][C:35](=[O:36])[C:34]2[CH:38]=[CH:39][CH:40]=[C:32]([C:31]([F:30])([F:41])[F:42])[CH:33]=2)[CH2:7][CH2:6][N:5]([CH:8]([CH3:28])[CH2:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:4]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 67928771trans-4-amino-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide

Product 1

HCID 67928763trans-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-4-[[3-(trifluoromethyl)benzoyl]amino]-1-piperidinebutanamideYield 86.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred and cooled solution of 4 parts of trans-4-amino-3-hydroxy-N,N,γ-trimethyl-α,αdiphenyl-1-piperidinebutanamide in 120 parts of trichloromethane were added 1.26 parts of N,N-diethylethanamine. A solution of 2.3 parts of 3-(trifluoromethyl)benzoyl chloride in 75 parts of trichloromethane was added dropwise. Upon completion, the reaction mixture was stirred overnight at room temperature. A solution of sodium carbonate in water was added. The separated organic layer was washed with water, dried, filtered and evaporated. The residue was taken up in 2,2'-oxybispropane. The precipitated product was filtered off and dried in vacuo at 60° C., yielding 4.9 parts (86.3%) of trans-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-4-[[3-(trifluoromethyl)benzoyl]amino]-1-piperidinebutanamide; mp. 140.7° C. (compound 1).

Workup

  1. stirringUpon completion, the reaction mixture was stirred overnight at room temperature
  2. washThe separated organic layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe precipitated product was filtered off
  7. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-e573f253a5484472bf368ef0e328604a
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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