Water → 1-[7-[1-hydroxy-4-(1-piperidyl)butyl]-9H-fluoren-2-yl]-4-(1-piperidyl)butan-1-ol

HRID 1576963Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([C:25](=[O:35])[CH2:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:19][CH:20]=4)[CH2:15][C:14]=3[CH:13]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O>CO>[N:1]1([CH2:7][CH2:8][CH2:9][CH:10]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([CH:25]([CH2:26][CH2:27][CH2:28][N:29]5[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]5)[OH:35])=[CH:19][CH:20]=4)[CH2:15][C:14]=3[CH:13]=2)[OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 24.5 g (0.052 mole) of 2,7-bis(4-piperidinobutyryl)fluorene dissolved in 400 ml of methanol is cooled to -10°C. and 3.8 g (0.1 mole) of sodium borohydride is slowly added wih stirring. The reaction mixture is gradually permitted to come to room temperature and stirring continued for an additional 16 hours. The contents of the reaction mixture are poured into approximately 1 liter of water, and the resulting solid which forms is filtered, washed with water and recrystallized from a solution of benzene. Recrystallization from a benzene-ether mixture results in the preparation of α, α'-bis(3-piperidinopropyl)-2,7-fluorenedimethanol having a m.p. of 181.5°-4.0°C, λmaxEtOH 273, and E 1cm1% 592.

Workup

customto come to room temperature
stirringstirring
filtrationthe resulting solid which forms is filtered
washwashed with water
customrecrystallized from a solution of benzene
customRecrystallization from a benzene-ether mixture

Sources & evidence

ORD record: ord-869d862f5fbd4a468dc66d750aad6fda
Source dataset: uspto-grants-1976_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03983124

Reaction notes

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