Triethylamine → HCID 14074281, compound

HRID 1723032Notes

Reaction equation

C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1.Br[CH2:22][C:23]1[C:24]([CH3:35])=[N:25][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:27][CH:28]=1>C(COC)OC>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:22][C:23]3[C:24]([CH3:35])=[N:25][C:26]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[N:27][CH:28]=3)[CH2:17][CH2:16]2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 1.05 g of triethylamine in 20 ml of absolute dimethoxyethane was added dropwise over 30 minutes with stirring to a mixture of 1.78 g (10 mmol) of 1-(4-hydroxyphenyl)piperazine, 3.05 g of 95% strength 5-bromomethyl-4-methyl-2-phenylpyrimidine (=11 mmol) and 80 ml of absolute 1,2-dimethoxyethane at 45° C. The mixture was stirred for a further 1 hour at 45° C. and 3 hours at 80° C., the solvent was evaporated in vacuo, the residue was taken up in CH2Cl2 water and neutralized to pH 6-7, the phases were separated, and the aqueous phase was extracted three times with CH2Cl2. The combined CH2Cl2 extracts were dried, filtered and evaporated in vacuo. The crystalline residue (3.7 g) was recrystallized from methanol. 2.35 g (65% of theory) of pure 4-(4-hydroxyphenyl)-1-(4 -methyl-2-phenylpyrimidin-5-ylmethyl)piperazine, melting point 201°-202° C., were obtained.

Workup

customthe solvent was evaporated in vacuo
customthe phases were separated
extractionthe aqueous phase was extracted three times with CH2Cl2
dry with materialThe combined CH2Cl2 extracts were dried
filtrationfiltered
customevaporated in vacuo
customThe crystalline residue (3.7 g) was recrystallized from methanol

Sources & evidence

ORD record: ord-69189070df8b47da8cc4149d16fff654
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04859670

Reaction notes

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