Triethylamine → HCID 21271727, compound

HRID 1194095Notes

Reaction equation

HRID 1194095 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][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:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH2:23]([O:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29]Br)[CH3:24].C(N(CC)CC)C>C(#N)C>[CH2:23]([O:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29][N:19]1[CH2:18][CH2:17][C:16]2[C:21](=[CH:22][C:13]([S:10](=[O:12])(=[O:11])[NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=3)=[CH:14][CH:15]=2)[CH2:20]1)[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76300Ethyl 4-bromobutyrateHCID 12606941HCID 12606941, compound

Product 1

HCID 21271727HCID 21271727, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.05 g, 8 mmol), ethyl-4-bromobutyrate (1.56 g), and triethylamine (0.81 g, 8 mmol) in acetonitrile (35 ml) was heated at 55°-60° for 4 hr. The mixture was filtered, the filtrate concentrated and chromatographed (silica gel, ether) to give ethyl-4-[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]butyrate (0.59 g, 17%) as an oil.

Workup

  1. temperaturewas heated at 55°-60° for 4 hr
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customchromatographed (silica gel, ether)

Sources & evidence

ORD record
ord-1ab493756e314d12977ad8f33828372b
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

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