Ammonium Hydroxide → 4-Piperidinecarboxamide, 4-(phenylamino)-1-(2-phenylethyl)-

HRID 1973785Notes

Reaction equation

HRID 1973785 reaction equation
[C:1]1([NH:7][C:8]2([C:22]#[N:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:24].[NH4+]>>[C:1]1([NH:7][C:8]2([C:22]([NH2:23])=[O:24])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 828001STK366646

Product 1

HCID 110237524-Piperidinecarboxamide, 4-(phenylamino)-1-(2-phenylethyl)-

Procedure

To 4500 parts of sulfonic acid are added portionwise 710 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarbonitrile, while keeping the temperature below 25° C. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is poured onto a mixture of 10.000 parts of crushed ice and 3600 parts of ammonium hydroxide. The product is extracted with trichloromethane (7500 parts). The extract is dried, filtered and evaporated. The residue is stirred in 140 parts of 2,2'-oxybispropane. The product is filtered off and dried, yielding 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxamide; mp. 182.5° C.

Workup

  1. customthe temperature below 25° C
  2. extractionThe product is extracted with trichloromethane (7500 parts)
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. stirringThe residue is stirred in 140 parts of 2,2'-oxybispropane
  7. filtrationThe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-e64e6b36ca2546029fc5893aa90e79a8
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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