Chloroform → trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamide

HRID 981301Notes

Reaction equation

HRID 981301 reaction equation
[CH3:1][O:2][C@H:3]1[C@H:8]([NH2:9])[CH2:7][CH2:6][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1.ClC(Cl)Cl.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C(N(CC)CC)C>[CH3:1][O:2][C@H:3]1[C@H:8]([NH:9][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=2)[CH2:7][CH2:6][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 13677827trans-3-Methoxy-1-(phenylmethyl)-4-piperidinamine

Product 1

HCID 67928762trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamideYield 80.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

To a stirred solution of 10 parts of trans-3-methoxy-1-(phenylmethyl)-4-piperidinamine and 5.95 parts of N,N-diethylethanamine in 75 parts of trichloromethane was added dropwise a solution of 10.4 parts of 3-(trifluoromethyl)benzoyl chloride in 15 parts of N,N-diethylethanamine while cooling in an ice bath. Upon completion, stirring was continued for 20 hours at room temperature. The mixture was washed twice with a sodium hydroxide solution 5% and once with water and then dried, filtered and evaporated in vacuo. After crystallization of the residue from 27 parts of methylbenzene, the product was filtered off, washed with 45 parts of methylbenzene and dried, yielding 14.4 parts (80.9%) of trans-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-3-(trifluoromethyl)benzamide; mp. 135.2° C. (interm. 8).

Workup

  1. temperaturewhile cooling in an ice bath
  2. washThe mixture was washed twice with a sodium hydroxide solution 5% and once with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customAfter crystallization of the residue from 27 parts of methylbenzene
  7. filtrationthe product was filtered off
  8. washwashed with 45 parts of methylbenzene
  9. customdried

Sources & evidence

ORD record
ord-2b7d0ae2b55344c7957c12646d94faaf
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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