Water → Ethyl 4-[[4-dimethylamino-2-pyrimidinyl]methylamino]-1-piperidinecarboxylate

HRID 1274996

Reaction equation

[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl[C:15]1[N:20]=[C:19]([N:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][N:16]=1.O>ClC(Cl)Cl>[CH3:22][N:21]([CH3:23])[C:19]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:1][NH:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]2)[N:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of ethyl 4-(methylamino)-1-piperidinecarboxylate (111.75 g) and 2-chloro-N,N-dimethyl-4-pyrimidinamine (47.3 g) is stirred and heated in an oil-bath for 22 hours at 120° C. The reaction mixture is cooled and the product is taken up in trichloromethane (500 ml). Water (300 ml) is added and the layers are separated. The organic phase is washed with water (200 ml), dried, filtered and evaporated. The residue solidifies on triturating in petroleumether. The product is filtered off and crystallized from diisopropyl ether (390 ml). After cooling to 0° C., the product is filtered off and dried, yielding 55.5 g (59.7%) of ethyl 4-[[4-dimethylamino-2-pyrimidinyl]methylamino]-1-piperidinecarboxylate (intermediate 1).

Workup

temperatureThe reaction mixture is cooled
customthe layers are separated
washThe organic phase is washed with water (200 ml)
customdried
filtrationfiltered
customevaporated
customon triturating in petroleumether
filtrationThe product is filtered off
customcrystallized from diisopropyl ether (390 ml)
temperatureAfter cooling to 0° C.
filtrationthe product is filtered off
customdried

Sources & evidence

ORD record: ord-3203bd07586e4b56911f5f6f004a41ea
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159982

Linked notes

Loading…