5-(3,4-Dichlorophenyl)-5-[3-(tetrahydropyran-4-yloxy)-propyl]-2-piperidone → 3-(3,4-Dichlorophenyl)-3-[3-(tetrahydropyran-4-yloxy)-propyl]-piperidine

HRID 2303945Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:16][CH2:17][CH2:18][O:19][CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH2:14][NH:13][C:12](=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:16][CH2:17][CH2:18][O:19][CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH2:10][CH2:11][CH2:12][NH:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 60 °C

Procedure

Piperidone (6) (42.9 g, 0.111 mol) in dry THF (300 mL) was added to a suspension of LAH (8.4 g, 0.222 mol) in dry THF (500 mL), which was then heated under N2 at 60° C. in an oil bath for 5 hours, then cooled and stirred at room temperature overnight (20 hours). The reaction was quenched by H2O (8.5 mL), 4N NaOH (8.5 mL), and H2O (0.5 mL), respectively. White solid was filtered and washed with Et2O. The filtrate was concentrated, and the crude oil was purified by flash chromatography (CH2Cl2—MeOH/95:5) to give a colorless oil (37.94 g 91.8%).

Workup

temperaturecooled
customThe reaction was quenched by H2O (8.5 mL), 4N NaOH (8.5 mL), and H2O (0.5 mL)
filtrationWhite solid was filtered
washwashed with Et2O
concentrationThe filtrate was concentrated
customthe crude oil was purified by flash chromatography (CH2Cl2—MeOH/95:5)
customto give a colorless oil (37.94 g 91.8%)

Sources & evidence

ORD record: ord-6a2b431000764bddbaf9464dfba2639f
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06433178B1

Reaction notes

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