Benzyl Chloride → HCID 67922776, compound

HRID 1110390Notes

Reaction equation

HRID 1110390 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6][N:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:4]1.Cl[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC1C=CC=CC=1>[C:11]1([CH2:10][N:9]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:8]2[CH2:7][CH2:6][N:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:4][C@H:3]2[O:2][CH3:1])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 13677741Ethyl cis-3-methoxy-4-[(phenylmethyl)amino]-1-piperidinecarboxylate

Product 1

HCID 67922776HCID 67922776, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 183.4 parts of ethyl cis-3-methoxy-4-[(phenylmethyl)amino]-1-piperidinecarboxylate, 144 parts of (chloromethyl)benzene, 85 parts of sodium carbonate and 720 parts of methylbenzene was stirred for 10 days at reflux temperature. The reaction mixture was filtered and the filtrate was washed three times with 400 parts of water, dried, filtered and evaporated. Petroleumether was added. The whole was cooled whereupon the product solidified. It was filtered off and crystallized from petroleumether. The product was filtered off and dried in vacuo at 40° C., yielding 155 parts (64%) of ethyl cis-4-[bis(phenylmethyl)amino]-3-methoxy-1-piperidinecarboxylate; mp. 95.2° C. (int. 46).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed three times with 400 parts of water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. additionPetroleumether was added
  8. temperatureThe whole was cooled whereupon the product
  9. filtrationIt was filtered off
  10. customcrystallized from petroleumether
  11. filtrationThe product was filtered off
  12. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-bf36a41cb21845ccb52c1be4071f431b
Source dataset
uspto-grants-1990_12
Patent number
US04975439

Reaction notes

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