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Methyl iodide → Methyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylate

HRID 1973774
Notes
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Reaction equation

HRID 1973774 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+].[CH3:25]N(C)P(=O)(N(C)C)N(C)C.IC>CC1C=CC=CC=1>[C:1]1([NH:7][C:8]2([C:21]([O:23][CH3:25])=[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 2724432Sodium 1-benzyl-4-(phenylamino)piperidine-4-carboxylate

Product 1

HCID 2724430Methyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 66.4 parts of sodium 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate in 375 parts of hexamethylphosphoric triamide is heated to 70° C. After cooling to 10° C, 31.2 parts of iodomethane are added (slightly exothermic reaction). The whole is stirred for 21 hours at room temperature. The reaction mixture is diluted with 360 parts of methylbenzene. The whole is washed with water and the layers are separated. The aqueous phase is washed with methylbenzene. The combined organic layers are washed successively once with 300 parts of a 10% sodium hydroxide solution and twice with 300 parts of water, dried, filtered and evaporated, yielding methyl 4-(phenylamino)-1 (phenylmethyl)-4-piperidinecarboxylate as a residue.

Workup

  1. temperatureAfter cooling to 10° C
  2. customslightly exothermic reaction)
  3. washThe whole is washed with water
  4. customthe layers are separated
  5. washThe aqueous phase is washed with methylbenzene
  6. washThe combined organic layers are washed successively once with 300 parts of a 10% sodium hydroxide solution and twice with 300 parts of water
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-0da7ba71bd384637b6703781501d4d97
Source dataset
uspto-grants-1976_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03998834

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes