Triethylamine → N-(3,4-Dimethoxybenzenesulphonyl)-1,2,3,4-tetrahydroquinoline

HRID 2142

Reaction equation

HRID 2142 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([S:21](Cl)(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].C(N(CC)CC)C>ClCCl>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([S:21]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)(=[O:22])=[O:23])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 694601,2,3,4-TetrahydroquinolineHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 667562N-(3,4-Dimethoxybenzenesulphonyl)-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,2,3,4-Tetrahydroquinoline (0.29 ml) was added to a suspension of 3,4-dimethoxybenzene sulphonyl chloride (0.50 g) in dichloromethane (15 ml) at room temperature. Triethylamine (0.44 ml) was added and the resulting mixture stirred for 24 hours at room temperature. The reaction mixture was then diluted with dichloromethane (20 ml) and washed successively with saturated aqueous sodium hydrogen carbonate solution (10 ml), 2N hydrochloric acid (10 ml) and saturated aqueous sodium chloride solution (10 ml). Drying over magnesium sulphate and concentration in vacuo provided a yellow oil. Purification by column chromatography eluting with 30% ethyl acetate in hexane provided the title compound as a colourless oil (0.60 g) which solidified on standing.

Workup

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate solution (10 ml), 2N hydrochloric acid (10 ml) and saturated aqueous sodium chloride solution (10 ml)
  2. dry with materialDrying over magnesium sulphate and concentration in vacuo
  3. customprovided a yellow oil
  4. customPurification by column chromatography
  5. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-80b4d3c6a338477cbce6e4a97e49acd8
Source dataset
uspto-grants-1998_03
Patent number
US05728712

Linked notes

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