Acetonitrile → 1-(t-Butoxycarbonyl)-4-(3-benzyl-1-ethyl-(1H)-pyrazol-5-yl)piperidine

HRID 278267Notes

Reaction equation

C(#N)C.[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=O)[CH2:18][C:19](=O)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[CH2:29]([NH:31][NH2:32])[CH3:30]>O>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[N:31]([CH2:29][CH3:30])[N:32]=[C:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=2)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 19 °C

Procedure

A 100 L cylindrical flask with a bottom valve was equipped with a mechanical stirrer, internal heating coil, 5 L dropping funnel, and thermocouple was charged with the acetonitrile (39 L) and 1-(1-(t-butoxycarbonyl)piperidin-4-yl)-4-phenylbutane-1,3-dione 4 (3.00 Kg, 8.68 mol). To the resulting clear light yellow solution was added water (18.6 l). The mixture was warmed to 19° C. and the mixture became clear. An ethyl hydrazine solution (35% in water, 1.66 Kg, 1.71 L, 9.55 mol) was added via a dropping funnel over 100 min. The batch temperature after the addition was 20° C. The reaction solution was aged for 1 h at 20 □ C then checked for completion by HPLC. If any 4 remained, additional ethyl hydrazine was added to complete the reaction. At the end of reaction the ratio of products 5:6:7 is 83.6:14.3:2.1 with complete consumption of 4.

Workup

customA 100 L cylindrical flask with a bottom valve was equipped with a mechanical stirrer
additionThe batch temperature after the addition
customwas 20° C
customthe reaction
customAt the end of reaction the ratio of products 5:6:7
customwith complete consumption of 4

Sources & evidence

ORD record: ord-f3124d2b52904bb1a661489ad4032e6c
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358979B1

Reaction notes

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