Carbon Dioxide → HCID 21428744, compound

HRID 437550Notes

Reaction equation

HRID 437550 reaction equation
[CH2:1]1[O:3][CH2:2]1.C(=O)=O.[F:7][C:8]([F:34])([F:33])[S:9]([C:12]1[CH:13]=[CH:14][C:15]2[CH:21]=[CH:20][C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=3[C:17](=[C:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[C:16]=2[CH:32]=1)(=[O:11])=[O:10]>CO.C(Cl)(Cl)Cl>[OH:3][CH:1]([N:29]1[CH2:30][CH2:31][C:26](=[C:17]2[C:16]3[CH:32]=[C:12]([S:9]([C:8]([F:34])([F:7])[F:33])(=[O:11])=[O:10])[CH:13]=[CH:14][C:15]=3[CH:21]=[CH:20][C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]2=3)[CH2:27][CH2:28]1)[CH3:2]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 6354Ethylene Oxide2×HCID 21428749HCID 21428749, compound

Product 1

HCID 21428744HCID 21428744, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of 0.244 g. of ethylene oxide of 30 ml. of methanol at dry-ice temperature is added to an ice cold solution of 2.55 g. of 4-(3-trifluoromethylsulfonyl-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine in 15 ml. of chloroform and 75 ml. of methanol. The solution is stirred at ambient temperature overnight. A second quantity (0.25 g.) of ethylene oxide is added as before and the mixture is again stirred overnight. The mixture is concentrated to dryness and the residue is coevaporated in vacuo several times with acetonitrile. The product is recrystallized several times from acetonitrile to give (±)-1-hydroxyethyl-4-(3-trifluoromethylsulfonyl-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, m.p. 141°-144° C.

Workup

  1. waitis again stirred overnight
  2. concentrationThe mixture is concentrated to dryness
  3. customThe product is recrystallized several times from acetonitrile

Sources & evidence

ORD record
ord-9121c0184520464c9909e0e64fef188f
Source dataset
uspto-grants-1977_06
Patent number
US04031222

Reaction notes

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