Propylamine → 8-chloro-2-(N-n-propylamino)tetralin

HRID 274800

Reaction equation

HRID 274800 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=O)[CH2:8][CH2:7]2.[CH2:13]([NH2:16])[CH2:14][CH3:15].[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH2:13]([NH:16][CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 4311764Sodium borohydrideHCID 46232698-Chloro-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 149692298-chloro-2-(N-n-propylamino)tetralin

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8-Chloro-2-tetralone (500 mg, 2.78 mMol) in toluene (25 mL) was reacted with propylamine (1.14 mL, 13.9 mMol) and sodium borohydride (500 rag) as described in Example2 to give after purification by flash chromatography (5% methanol in dichloromethane+tr. NH4OH) the title compound as a dark oil (340 mg, 55%). The hydrochloride was formed, and recrystallization (ethanol/diethyl ether) gave a colorless, crystalline solid (m.p.=213°-215° C.).

Workup

  1. customto give
  2. customafter purification by flash chromatography (5% methanol in dichloromethane+tr. NH4OH) the title compound as a dark oil (340 mg, 55%)

Sources & evidence

ORD record
ord-9d681bdd390848d68b15aa5fbf35ee22
Source dataset
uspto-grants-1995_02
Patent number
US05389687

Linked notes

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