Water → Propyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate ethanedioate

HRID 1448272Notes

Reaction equation

HRID 1448272 reaction equation
[C:1]1([NH:7][C:8]2([C:21]([O-:23])=[O:22])[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].Br[CH2:26][CH2:27][CH3:28].CC1C=CC=CC=1.[OH2:36].CN(C)P(=[O:46])(N(C)C)N(C)C>>[C:21]([OH:23])(=[O:22])[C:8]([OH:46])=[O:36].[C:1]1([NH:7][C:8]2([C:21]([O:23][CH2:26][CH2:27][CH3:28])=[O:22])[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 78401-BromopropaneHCID 12679HexamethylphosphoramideHCID 2724432Sodium 1-benzyl-4-(phenylamino)piperidine-4-carboxylate

Product 1

HCID 12298153Propyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate ethanedioate

Conditions

Temperature
10 °C

Procedure

100 parts of sodium 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate are dissolved in 565 parts of anhydrous hexamethylphosphoric triamide at 70°-80° C. The solution is cooled to 10° C. and 40.6 parts of 1-bromopropane are added dropwise. Upon completion, stirring is continued for 25 hours at room temperature. Then there are added methylbenzene and water. The organic phase is separated, washed successively with water, 10% of sodium hydroxide solution and again with water, dried, filtered and evaporated. The residue is dissolved in hexane and the solution is allowed to stand overnight at room temperature. It is filtered and the filtrate is evaporated. The residue is converted into the ethanedioate salt in 2-propanone. The salt is filtered off and dried, yielding propyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate ethanedioate; mp. 192.2° C.

Workup

  1. customThe organic phase is separated
  2. washwashed successively with water, 10% of sodium hydroxide solution and again with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue is dissolved in hexane
  7. waitto stand overnight at room temperature
  8. filtrationIt is filtered
  9. customthe filtrate is evaporated
  10. filtrationThe salt is filtered off
  11. customdried

Sources & evidence

ORD record
ord-40823f4011fe4aaf96569833e8262fc8
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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