Triethylamine → HCID 20068665, compound

HRID 981984Notes

Reaction equation

HRID 981984 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][N:20]([C:23]4(SC)[N:28]=[CH:27][C:26]([F:29])=[CH:25][NH:24]4)[CH2:19][CH2:18]3)[O:13][CH2:12][CH2:11][O:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C>[Ni].O.CCO>[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][N:20]([C:23]4[N:24]=[CH:25][C:26]([F:29])=[CH:27][N:28]=4)[CH2:21][CH2:22]3)[O:10][CH2:11][CH2:12][O:13]2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 20068643HCID 20068643, compound

Product 1

HCID 20068665HCID 20068665, compoundYield 23.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]-4-(5-fluoro-2-methylthio-2-pyrimidinyl)piperazine hydrochloride (7.45 g, 0.0.17 mole), triethylamine (3.05 g, 0.034 mole) and 2 teaspoons of Raney Nickel in water were mixed in EtOH (125 mL) and refluxed 18 h. The hot reaction mixture was filtered and the filtrate was concentrated in vacuo to about 1/5 volume. A crude crystalline product was obtained by filtration and its recrystallization from 20-25 mL EtOH gave 1.6 g of solid, m.p. 220°-222° C. This solid was converted to the hydrochloride salt in EtOH using ethanolic HCl. Filtration and drying gave 1.6 g of product, m.p. 242°-244° C.

Workup

  1. temperaturerefluxed 18 h
  2. filtrationThe hot reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to about 1/5 volume
  4. customA crude crystalline product was obtained by filtration and its recrystallization from 20-25 mL EtOH

Sources & evidence

ORD record
ord-5f9e8c277af945feac9aab8ee44f73fe
Source dataset
uspto-grants-1991_02
Patent number
US04994460

Reaction notes

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