Hydrochloric Acid → 7-(Indole-1-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline Hydrochloride

HRID 22823Notes

Reaction equation

HRID 22823 reaction equation
[N:1]1([S:10]([C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][N:19](C(=O)C)[CH2:20]3)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[ClH:26]>C(O)CCC>[ClH:26].[N:1]1([S:10]([C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][NH:19][CH2:20]3)=[CH:15][CH:14]=2)(=[O:11])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 225920211-[7-(Indole-1-sulfonyl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone

Product 1

HCID 102692627-(Indole-1-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline HydrochlorideYield 72%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1-[7-(indole-1-sulfonyl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone (D1) (12 g, 34 mmol) in 3M hydrochloric acid (200 ml) and n-butanol (100 ml) was refluxed for 7 h. The reaction mixture was evaporated in vacuo to dryness and the residue was recrystallized from 2-propanol/diethyl ether to give the title compound (E1) (8.5 g, 72%), NMR (D6-DMSO) 3.03 (2H, t, J=6.0 Hz), 3.29 (2H, t, J=6.0 Hz), 4.29 (2H, s), 6.85 (1H, d, J=3.7 Hz), 7.22-7.43 (3H, m), 7.60 (1H, d, J=7.6 Hz), 7.79-7.85 (2H, m), 7.94-8.01 (2H, m); MS: m/z (MH+) 313.

Workup

  1. temperaturewas refluxed for 7 h
  2. customThe reaction mixture was evaporated in vacuo to dryness
  3. customthe residue was recrystallized from 2-propanol/diethyl ether

Sources & evidence

ORD record
ord-1d8a295f90094d2b813a604800cdcb94
Source dataset
uspto-grants-2005_02
Patent number
US06849644B2

Reaction notes

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