Propylamine → 3-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)-N-propylpropane-1-sulfonamide

HRID 242089Notes

Reaction equation

HRID 242089 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH2:27][CH2:28][CH2:29][S:30](Cl)(=[O:32])=[O:31])[CH:24]=4)[CH2:19][CH2:18][N:17]=3)[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1>ClCCl>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH2:27][CH2:28][CH2:29][S:30]([NH:4][CH2:1][CH2:2][CH3:3])(=[O:32])=[O:31])[CH:24]=4)[CH2:19][CH2:18][N:17]=3)[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 582461963-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)propane-1-sulfonyl chloride

Product 1

HCID 582462893-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)-N-propylpropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1-Propylamine (314 mg, 5.31 mmol) was dissolved in dichloromethane (3 mL) and a solution of 3-({1-[1-(4-chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)propane-1-sulfonyl chloride (200 mg, 0.442 mmol) in dichloromethane (2 mL) was added dropwise. After 1 h stirring at room temperature the reaction mixture was diluted with dichloromethane (10 mL) and was washed with aqueous ammonium chloride solution (2×) and water (1×), dried (MgSO4) and concentrated in vacuo. The crude product (265 mg) was used for the next step without purification.

Workup

  1. washwas washed with aqueous ammonium chloride solution (2×) and water (1×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product (265 mg) was used for the next step without purification

Sources & evidence

ORD record
ord-c843e2115e104c0f8a0854116b8f0bea
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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