Pyridine → 2-Acetyl-5-phenylsulphonamido-1,2,3,4-tetrahydroisoquinoline

HRID 1194102Notes

Reaction equation

HRID 1194102 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:14])[CH2:5]1)(=[O:3])[CH3:2].N1C=CC=CC=1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:14][S:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:29])=[O:28])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 212717261-(5-amino-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Product 1

HCID 212717242-Acetyl-5-phenylsulphonamido-1,2,3,4-tetrahydroisoquinolineYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-acetyl-5-amino-1,2,3,4-tetrahydroisoquinoline (6.6 g) in a mixture of dry pyridine (3 g) and dichloromethane (450 ml) at approximately 5° C. was added dropwise, over 15 minutes, benzenesulphonyl chloride (6.2 g). The orange solution was stirred overnight at room temperature and was then washed several times with water, dried and the solvent was then evaporated to give a dark orange oil. Crystallisation from 2-propanol gave 2-acetyl-5-phenylsulphonamido-1,2,3,4-tetrahydroisoquinoline as a pale pink solid (9.5 g) m.p. 131°-132° C.

Workup

  1. additionwas added dropwise, over 15 minutes
  2. washwas then washed several times with water
  3. customdried
  4. customthe solvent was then evaporated
  5. customto give a dark orange oil
  6. customCrystallisation from 2-propanol

Sources & evidence

ORD record
ord-87293aca5f094c7ba142a0ccfef0d8d5
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

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