Benzene → HCID 20371569, compound

HRID 616222Notes

Reaction equation

HRID 616222 reaction equation
[CH2:1]([O:3]C(Cl)=O)[CH3:2].[CH:7]1[C:17]2[C:16](=[C:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[CH2:13][O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[CH:29]1C=CC=CC=1>>[CH:7]1[C:17]2[C:16](=[C:18]3[CH2:19][CH2:20][N:21]([CH2:24][CH2:2][C:1](=[O:3])[CH3:29])[CH2:22][CH2:23]3)[C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[CH2:13][O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 241Benzene2×HCID 10928Ethyl chloroformateHCID 14175796HCID 14175796, compound

Product 1

HCID 20371569HCID 20371569, compound

Procedure

A solution of 96 g of chloroformic acid ethyl ester in 100 cc of benzene is added dropwise to a solution of 64 g of 4-(6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)-1-methylpiperidine in 600 cc of benzene, and the mixture is heated in an oil bath of 100° for 4 hours. After cooling, the reaction mixture is filtered through diatomaceous earth, the filtrate is extracted with 2 N hydrochloric acid and water, dried over magnesium sulphate and completely concentrated at reduced pressure. The resulting urethane is split in a manner analogous to that described in Example 4 a), whereby crude 4-(6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)piperidine is obtained as yellow-brown oil.

Workup

  1. temperaturethe mixture is heated in an oil bath of 100° for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered through diatomaceous earth
  4. extractionthe filtrate is extracted with 2 N hydrochloric acid and water
  5. dry with materialdried over magnesium sulphate
  6. concentrationcompletely concentrated at reduced pressure
  7. customThe resulting urethane is split in a manner analogous to
  8. customis obtained as yellow-brown oil

Sources & evidence

ORD record
ord-e08a88158c484384bbc3581163a3adae
Source dataset
uspto-grants-1978_02
Patent number
US04072756

Reaction notes

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