1-Bromo-3-chloropropane → 2-(3-Chloropropyl)-7-(morpholin-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinoline

HRID 394457

Reaction equation

HRID 394457 reaction equation
[N:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][NH:16][CH2:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:28][CH2:29][CH2:30][Cl:31]>CN(C=O)C>[Cl:31][CH2:30][CH2:29][CH2:28][N:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][C:10]([S:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)(=[O:9])=[O:8])=[CH:11][CH:12]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 219836637-(Morpholine-4-sulfonyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 181765112-(3-Chloropropyl)-7-(morpholin-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolineYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

1.2 g (4.4 mmol) of 7-(morpholin-4-ylsulfonyl)-1,2,3,4-tetra-hydroisoquinoline and 1.0 g (10 mmol) of triethylamine were dissolved in DMF at 40° C., 1.1 g (6.6 mmol) of 1-bromo-3-chloropropane were added dropwise, and the mixture was stirred at 40° C. for 3 h. For workup, the mixture was concentrated, and the residue was taken up in water and extracted with methyl tert-butyl ether. Drying over sodium sulfate, filtration and removal of the solvent were followed by purification by chromatography (silica gel; mobile phase: methylene chloride with 2% methanol) to afford 0.7 g (2 mmol) of a pale oil.

Workup

  1. concentrationFor workup, the mixture was concentrated
  2. extractionextracted with methyl tert-butyl ether
  3. dry with materialDrying over sodium sulfate, filtration and removal of the solvent
  4. customwere followed by purification by chromatography (silica gel; mobile phase: methylene chloride with 2% methanol)

Sources & evidence

ORD record
ord-47ac1345935440fc89bfcfc31a7fbf21
Source dataset
uspto-grants-2003_08
Patent number
US06602867B1

Linked notes

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