Acetone → N-phenylcarbamoyl-1,2,3,4-tetrahydroisoquinoline

HRID 1903287Notes

Reaction equation

HRID 1903287 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.CC(C)=O.[SH2]=N.[C:17]1([NH:23][C:24](C2C=CC=CC=2C(O)=O)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[C:17]1([NH:23][C:24]([N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 180Acetone2×HCID 70461,2,3,4-TetrahydroisoquinolineHCID 178514671HCID 178514671, compound

Product 1

HCID 808385N-phenylcarbamoyl-1,2,3,4-tetrahydroisoquinolineYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 1.35 g 1,2,3,4-tetrahydroisoquinoline with 5 ml aceton was added dropwise to a suspension of 1.5 g phenylcarbamoyl-benzoic acid sulfimide with 20 ml aceton, at ambient temperature. The reaction mixture was stirred for 45 minutes, then diluted with 150 ml water, cooled to 5° C. and the precipitated crystalline product was filtered, washed with water and dried. 1.18 g N-phenylcarbamoyl-1,2,3,4-tetrahydroisoquinoline was obtained with a melting point of 145°-146° C.

Workup

  1. filtrationthe precipitated crystalline product was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-4c2b4ee5166d49318ed603cca3cf3189
Source dataset
uspto-grants-1984_03
Patent number
US04435567

Reaction notes

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