Sulfuric Acid → 4-Piperidinecarboxamide, 4-(phenylamino)-1-(2-phenylethyl)-

HRID 1448283Notes

Reaction equation

HRID 1448283 reaction equation
S(=O)(=O)(O)O.[C:6]1([NH:12][C:13]2([C:27]#[N:28])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-:29].[NH4+]>>[C:6]1([NH:12][C:13]2([C:27]([NH2:28])=[O:29])[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 828001STK366646

Product 1

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

Procedure

To 4500 parts of sulfuric 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-53d6852cd58c4cefb95434cad131f887
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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