Dichloromethane → HCID 86744581, compound

HRID 981316Notes

Reaction equation

HRID 981316 reaction equation
[NH2:1][C:2]1[C:3]([Cl:42])=[CH:4][C:5]([O:40][CH3:41])=[C:6]([CH:39]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][N:13]([CH:16]([CH3:36])[CH2:17][C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:12][C@H:11]1[O:37][CH3:38])=[O:8].ClCCl.[C:46](Cl)(=[O:50])[CH2:47][CH2:48][CH3:49]>C(N(CC)CC)C>[Cl:42][C:3]1[C:2]([NH:1][C:46](=[O:50])[CH2:47][CH2:48][CH3:49])=[CH:39][C:6]([C:7]([NH:9][C@H:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:36])[CH2:17][C:18]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:19]([N:21]([CH3:22])[CH3:23])=[O:20])[CH2:12][C@H:11]2[O:37][CH3:38])=[O:8])=[C:5]([O:40][CH3:41])[CH:4]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8855Butyryl chlorideHCID 86744582HCID 86744582, compound

Product 1

HCID 86744581HCID 86744581, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 6.52 parts of cis-4-[(5-amino-4-chloro-2-methoxybenzoyI)amino]-3-methoxy-N,N,γ-trimethyl-α,α-diphenyl-1piperidinebutanamide in 195 parts of dichloromethane were added 2.6 parts of butanoyl chloride. After stirring for 15 minutes, 2.94 parts of N,N-diethylethanamine were added. The whole was stirred overnight at room temperature. The reaction mixture was washed successively with a sodium carbonate solution and water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was stirred in 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.39 parts (46.5%) of cis-4-[[4-chloro-2-methoxy-5-[(1-oxobutyl)amino]benzoyl]amino]-3-methoxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide; mp. 130.7° C. (compound 65).

Workup

  1. stirringThe whole was stirred overnight at room temperature
  2. washThe reaction mixture was washed successively with a sodium carbonate solution and water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. stirringThe residue was stirred in 2,2'-oxybispropane
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-ee46136828d84cfb99814d20d7d8c559
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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