Lithium Hydroxide → 4-(1-Piperidinesulfonylpiperidin-4-ylmethyl)-phenylamine

HRID 723594Notes

Reaction equation

FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([S:19]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[CH:8][CH:7]=1)=O.[OH-].[Li+]>CO.O>[N:22]1([S:19]([N:16]2[CH2:15][CH2:14][CH:13]([CH2:12][C:9]3[CH:10]=[CH:11][C:6]([NH2:5])=[CH:7][CH:8]=3)[CH2:18][CH2:17]2)(=[O:21])=[O:20])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2,2,2-trifluoro-N-[4-(1-piperidinesulfonylpiperidin-4-ylmethyl)-phenyl]acetamide (0.48 g, 1.11 mmol) and lithium hydroxide (0.23 g, 5.54 mmol) in methanol (10 mL) and water (1 mL) was heated at 60° C. for about 2 hours. The reaction mixture was concentrated in vacuo, diluted with water, and extracted with dichloromethane. The organic extracts were washed with water and brine, and dried (Na2SO4). The residue was crystallized from ethyl acetate/hexanes, to give 4-(1-piperidinesulfonylpiperidin-4-ylmethyl)-phenylamine (0.30 g) as a white solid, m.p. 144–145° C.; Analysis for C17H27N3O2S: Calc.: C, 60.50; H, 8.06; N, 12.45; Found: C, 60.76; H, 8.07; N, 12.56.

Workup

concentrationThe reaction mixture was concentrated in vacuo
additiondiluted with water
extractionextracted with dichloromethane
washThe organic extracts were washed with water and brine
dry with materialdried (Na2SO4)
customThe residue was crystallized from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-03acfee76c1c414ab6102a5540fe3d85
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141584B2

Reaction notes

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