1,2,3,4-Tetrahydroisoquinoline → HCID 20501316, compound

HRID 851470Notes

Reaction equation

HRID 851470 reaction equation
[C:1]([CH2:9][S:10]([C:13]1[CH:22]=[C:21]2[C:16]([CH2:17][CH2:18][NH:19][CH2:20]2)=[CH:15][CH:14]=1)(=O)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](N1CCC2C(=CC(S(Cl)(=O)=O)=CC=2)C1)(=[O:25])[CH3:24].C1C2C(=CC=CC=2)CCN1.C(N1CCC2C(=CC(S)=CC=2)C1)(=O)C>C(O)(=O)C.Cl>[C:23]([N:19]1[CH2:18][CH2:17][C:16]2[C:21](=[CH:22][C:13]([S:10][CH2:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:15]=2)[CH2:20]1)(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 126069042-Acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chlorideHCID 126069591-(3,4-Dihydro-7-mercapto-2(1H)-isoquinolinyl)ethanoneHCID 20501317HCID 20501317, compound

Product 1

HCID 20501316HCID 20501316, compound

Reagents, catalysts & solvents 1

HCID 22641269Acetate-hydrochloric acidSolvent

Procedure

The starting appropriately substituted tetrahydroisoquinolines of the formula (A) are conveniently prepared by standard reactions well known in the chemical arts as shown below: ##STR3## 2-Acetyl-7-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline, which is prepared by acylating and then chlorosulfonating 1,2,3,4-tetrahydroisoquinoline, is reduced to 2-acetal-7-mercapto-1,2,3,4-tetrahydroisoquinoline employing stannous chloride in acetic acid-hydrochloric acid mixture. The 2-acetyl-7-mercapto-1,2,3,4-tetrahydroisoquinoline is then condensed with the appropriately substituted α-bromo acetophenone to afford 2-acetyl-7-benzoylmethylthio-1,2,3,4-tetrahydroisoquinoline (B) which is then oxidized with m-chloroperbenzoic acid and hydrolyzed to yield the desired 7-benzoylmethylsulfonyl-1,2,3,4-tetrahydroisoquinoline (A). Bis(chlorosulfonyl)imide is prepared from chlorosulfonic acid and chlorosulfonylisocyanate.

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-d408c510949f466fa0a492e7b6a6f8d4
Source dataset
uspto-grants-1983_05
Patent number
US04385047

Reaction notes

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