Water → HCID 12298157, compound

HRID 1973808Notes

Reaction equation

HRID 1973808 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2([C:23]([OH:25])=[O:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[H-].[Na+].IC.[OH2:30].[CH3:31]N(C)P(=[O:40])(N(C)C)N(C)C>>[C:23]([OH:25])(=[O:24])[C:10]([OH:40])=[O:30].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2([C:23]([O:25][CH3:31])=[O:24])[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][CH2:15]2)=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 12298139HCID 12298139, compound

Product 1

HCID 12298157HCID 12298157, compound

Conditions

Temperature
15 °C

Procedure

55 Parts of 4-[(4-methoxyphenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxylic acid are dissolved in 400 parts of dry hexamethylphosphoric triamide at 95° C. The solution is cooled to 15° C and 4.8 parts of sodium hydride dispersion 78% are added. After stirring for 2 hours at room temperature, 26.5 parts of iodomethane are added dropwise at a temperature below 20° C. Upon completion, stirring is continued for 24 hours at room temperature. The reaction mixture is poured onto 600 parts of water and the product is extracted with methylbenzene. The extract is washed once with a sodium hydroxide solution 10% and twice with water, dried, filtered and evaporated. The residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and crystallized from 2-propanol, yielding methyl 4-[(4-methoxyphenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxylate ethanedioate; mp. 177°-185° C.

Workup

  1. stirringUpon completion, stirring
  2. waitis continued for 24 hours at room temperature
  3. extractionthe product is extracted with methylbenzene
  4. washThe extract is washed once with a sodium hydroxide solution 10% and twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe salt is filtered off
  9. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-0d3b74d4310a4a978fa4a4ffd20ba5e2
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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