Boron tribromide → 2-(N-n-propyl-N-2-[2-benzothienyl]ethylamino)-5-hydroxytetralin

HRID 1645930Notes

Reaction equation

HRID 1645930 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15]C)[CH2:6]1)[CH2:2][CH3:3].[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[CH2:26][C:27](O)=O.B(Br)(Br)Br>C1(C)C(C)=CC=CC=1>[CH2:1]([N:4]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:15])[CH2:6]1)[CH2:27][CH2:26][C:18]1[S:17][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 102425482-Propylamino-5-methoxytetralinHCID 127650652-(1-Benzothiophen-2-yl)acetic acid

Product 1

HCID 145805852-(N-n-propyl-N-2-[2-benzothienyl]ethylamino)-5-hydroxytetralin

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-(N-n-propylamino)-5-methoxytetralin, 2-benzothienyl acetic acid and trimethylaminoborohydride in dry xylene is refluxed under an atmosphere of nitrogen as described by Horn et al, Pharm. Weekbld. Sci. Ed. 7 208-211, 1985. The resulting methoxy intermediate is demethylated using boron tribromide as described in the above article to yield the desired product.

Workup

  1. temperatureis refluxed under an atmosphere of nitrogen

Sources & evidence

ORD record
ord-3e3e94b6c8374f5e8b414b751b75c351
Source dataset
uspto-grants-1993_01
Patent number
US05177112

Reaction notes

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