m-Chloroperbenzoic acid → HCID 23336529, compound

HRID 903563Notes

Reaction equation

HRID 903563 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([S:14][CH3:15])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([S:14]([CH3:15])=[O:24])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23336521HCID 23336521, compound

Product 1

HCID 23336529HCID 23336529, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N-acetyl-7-methylthio-1,2,3,4-tetrahydroisoquinoline, (2 gm., 0.009 m.) in 20 ml. of chloroform was cooled to -20° C. and treated with (1.6 gm., 0.009 m.) m-chloroperbenzoic acid. The reaction mixture was allowed to warm to 25° C. and was washed with 10% aqueous sodium carbonate, dried over sodium sulfate and evaporated to yield N-acetyl-7-methylsulfinyl-1,2,3,4-tetrahydroisoquinoline. This compound was hydrolyzed following the procedure set forth in Example 1 to yield 7-methylsulfinyl-1,2,3,4-tetrahydroisoquinoline hydrochloride, m.p. 200°-202° C. from ethanol-ethyl acetate.

Workup

  1. washwas washed with 10% aqueous sodium carbonate
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-933b3a597ae44d96b50fed84e6658f43
Source dataset
uspto-grants-1980_10
Patent number
US04228170

Reaction notes

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