Sulfuric Acid → HCID 86744271, compound

HRID 345605Notes

Reaction equation

HRID 345605 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:30]([C:31]#[N:32])=[CH:29][C:10]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][C@H:15]2[O:27][CH3:28])=[O:12])=[C:9]([O:33][CH3:34])[CH:8]=1.[OH-:35].[NH4+]>>[NH2:6][C:7]1[CH:8]=[C:9]([O:33][CH3:34])[C:10]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][C@H:15]2[O:27][CH3:28])=[O:12])=[CH:29][C:30]=1[C:31]([NH2:32])=[O:35]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 15096829HCID 15096829, compound

Product 1

HCID 86744271HCID 86744271, compound

Procedure

285 Parts of sulfuric acid were cooled in an ice-bath and 15.5 parts of cis-4-amino-5-cyano-2-methoxy-N-[3-methoxy-1-(phenylmethyl)-4-piperidinyl]benzamide were added portionwise while cooling. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was poured onto ice-water and the whole was alkalized with ammonium hydroxide. The product was filtered off and stirred in a mixture of trichloromethane and water. The product was filtered off again and dried, yielding 15.0 parts of cis-4-amino-6-methoxy-N1 -[3-methoxy-1-(phenylmethyl)-4-piperidinyl]-1,3-benzenedicarboxamide (compound 236).

Workup

  1. temperaturewhile cooling
  2. additionThe reaction mixture was poured onto ice-water
  3. filtrationThe product was filtered off
  4. stirringstirred in a mixture of trichloromethane and water
  5. filtrationThe product was filtered off again
  6. customdried

Sources & evidence

ORD record
ord-0d55d428824242268d14670011e8d93f
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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