Dipropylamine → 2-Di-n-propylamino-8-fluoro-1,2,3,4-tetrahydronaphthalene

HRID 274796Notes

Reaction equation

HRID 274796 reaction equation
[F: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]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15].[BH4-].[Na+]>>[CH2:13]([N:16]([CH2:17][CH2:18][CH3:19])[CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 8902DipropylamineHCID 41379018-Fluoro-2-tetraloneHCID 4311764Sodium borohydride

Product 1

HCID 152304892-Di-n-propylamino-8-fluoro-1,2,3,4-tetrahydronaphthaleneYield 33%

Procedure

8-Fluoro-2-tetralone (2.60 gm, 15.8 mMol) was reacted with dipropylamine (3.3 mL, 33 mMol) and sodium borohydride (1.5 gm) as described in Example 1 to give the title compound as a colorless oil (1.3 gm, 33%). The hydrochloride salt was formed and crystallization (ethanol/diethyl ether) gave colorless crystals (m.p.=164° C.).

Sources & evidence

ORD record
ord-9952f1340e614b9a8ce50284cf14a4ae
Source dataset
uspto-grants-1995_02
Patent number
US05389687

Reaction notes

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