Aluminium lithium hydride → 2-(4-(4-benzylpiperazin-1-yl)cyclohexyl)-N,N-dimethylethanamine

HRID 243563Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH:17]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=O)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][N:23]([CH3:24])[CH3:25])[CH2:16][CH2:15]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(4-(4-benzylpiperazin-1-yl)cyclohexyl)-N,N-dimethylacetamide (800 mg) is dissolved in THF (20 ml) and cooled to 0° C. 2 M LiAlH4 in THF (2.3 ml) is added. The reaction mixture is warmed to room temperature and stirred for 1 hour. The reaction is quenched by slow addition of satd. aqueous K2CO3 (50 ml), then a potassium sodium tartrate solution (20 ml) is added. The mixture is diluted with EtOAc and the layers are separated. The aqueous layer is extracted with EtOAc (2×). The combined organic layers are dried (Na2SO4), filtered, and the solvent is removed under reduced pressure to give 2-(4-(4-benzylpiperazin-1-yl)cyclohexyl)-N,N-dimethylethanamine (660 mg). m/z(+) 330 (M+H+).

Workup

temperatureThe reaction mixture is warmed to room temperature
customThe reaction is quenched by slow addition of satd
additionaqueous K2CO3 (50 ml), then a potassium sodium tartrate solution (20 ml) is added
additionThe mixture is diluted with EtOAc
customthe layers are separated
extractionThe aqueous layer is extracted with EtOAc (2×)
dry with materialThe combined organic layers are dried (Na2SO4)
filtrationfiltered
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-b2fb1a1e5fb2481d890213272a9e0e82
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653262B2

Reaction notes

Loading…