(+-)-Tetrahydropapaverine → HCID 13583877, compound

HRID 2118573Notes

Reaction equation

HRID 2118573 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:11][CH:12]2[NH:21][CH2:20][CH2:19][C:18]3[CH:17]=[C:16]([O:22][CH3:23])[C:15]([O:24][CH3:25])=[CH:14][C:13]2=3)=[CH:7][C:8]=1[O:9][CH3:10].[Cl:26][CH2:27][CH2:28][N:29]=[C:30]=[O:31]>C(Cl)(Cl)Cl>[CH3:10][O:9][C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:2][CH3:1])[CH2:11][CH:12]1[C:13]2[C:18](=[CH:17][C:16]([O:22][CH3:23])=[C:15]([O:24][CH3:25])[CH:14]=2)[CH2:19][CH2:20][N:21]1[C:30](=[O:31])[NH:29][CH2:28][CH2:27][Cl:26]

Participants

4

Reactant 2

HCID 5418(+-)-TetrahydropapaverineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 13583877HCID 13583877, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.86 g of tetrahydropapaverine are dissolved in 15 ml chloroform, then are added 0.7 ml of chlorethylisocyanate and the reaction mixture is stirred at ambient temmperature for 24 hours. The chloroform is distilled to dryness under vacuum. The thus obtained oily residue is suspended in ether and is left there to stay at a temperature about 0° C. for two days. A solid amorphous product is obtained that is filtered, washed several times with ether and dried at ambient temperature. Thus is prepared 1 g of compound 1c with melting point 73°-76° C.

Workup

  1. distillationThe chloroform is distilled to dryness under vacuum
  2. waitis left there
  3. waitto stay at a temperature about 0° C. for two days
  4. customA solid amorphous product is obtained
  5. filtrationthat is filtered
  6. washwashed several times with ether
  7. customdried at ambient temperature
  8. customThus is prepared 1 g of compound 1c with melting point 73°-76° C.

Sources & evidence

ORD record
ord-1c810abfc781417b885ea123b991b4a0
Source dataset
uspto-grants-1987_07
Patent number
US04678853

Reaction notes

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