Methyl Ethyl Ketone → HCID 70047982, compound

HRID 1419939Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([C:13]([NH:15][CH2:16][CH2:17]Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21][C:22]1([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([C:13]([NH:15][CH2:16][CH2:17][N:25]2[CH2:26][CH2:27][C:22]([OH:21])([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)[CH2:23][CH2:24]2)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-benzyloxy-N-(2-chloro-ethyl)-benzamide (2.0 g, 6.9 mmol), 4-hydroxy-4-(4-methyl-benzyl)-piperidine (1.06 g, 5.18 mmol), potassium carbonate (1.43 g, 10.35 mmol) and 2-butanone (40 ml) was stirred for 15 h at 60° C. After the addition of water, the mixture was extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica gel, methylene chloride methanol from 95:5 to 9:1) to give 4-benzyloxy-N-[2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-ethyl]-benzamide (445 mg, 19%) as a light yellow solid. MS: me/e =459 (M+H)+.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
customevaporated
customThe residue was purified by chromatography (silica gel, methylene chloride methanol from 95:5 to 9:1)

Sources & evidence

ORD record: ord-2a0d634d2f2a4ec8b0189d125974d914
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05889026

Reaction notes

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