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

HRID 1448271Notes

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>[CH3:25][O:22][C:21]([C:8]1([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:23]

Participants

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 methyl4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate as a residue.

Workup

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

Sources & evidence

ORD record: ord-1bb47b89dc7f4c2cb92133c4c969b130
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04179569

Reaction notes

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