1,2,3,4-Tetrahydroisoquinoline → HCID 178527374, compound

HRID 1681667Notes

Reaction equation

HRID 1681667 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.[NH:11]1[CH:15]=[C:14]([S:16](Cl)(=[O:18])=[O:17])[N:13]=[CH:12]1>C1(C)C=CC=CC=1>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[S:16]([C:14]1[N:13]=[CH:12][NH:11][CH:15]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 178527435HCID 178527435, compound

Product 1

HCID 178527374HCID 178527374, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,2,3,4-tetrahydroisoquinoline (13.22 g) and imidazole-4-sulphonyl chloride (7.57 g) in toluene (70 ml) was stirred for 1 hour and then allowed to stand overnight. It was evaporated and the residue partitioned between diethyl ether and aqueous sodium hydroxide. The aqueous layer was clarified by ether extraction and then acidified with concentrated hydrochloric acid. The precipitate was collected, washed with water and dried to give crude 4-(1,2,3,4-tetrahydroisoquinolin-2-ylsulphonyl)-1H-imidazole. A solution of this product (9 g) in dimethylformamide was treated with sodium hydride (1.13 g of 80% in oil), followed by dimethylsulphamoyl chloride (5.4 g). The mixture was stirred for 1 hour and poured into water. The precipitate was collected and worked up to give the starting material.

Workup

  1. customIt was evaporated
  2. customthe residue partitioned between diethyl ether and aqueous sodium hydroxide
  3. extractionThe aqueous layer was clarified by ether extraction
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e66914a0cc934a02b3d0d63c60495bc4
Source dataset
uspto-grants-1992_12
Patent number
US05173503

Reaction notes

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