Dimethylformamide → HCID 70045808, compound

HRID 1419943Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C=O)C.[CH3:35][NH:36][CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][C:42]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=2)([OH:45])[CH2:41][CH2:40]1>O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:36]([CH2:37][CH2:38][N:39]2[CH2:40][CH2:41][C:42]([OH:45])([CH2:46][C:47]3[CH:48]=[CH:49][C:50]([CH3:53])=[CH:51][CH:52]=3)[CH2:43][CH2:44]2)[CH3:35])=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-benzyloxy benzoic acid (265 mg, 1.16 mmol), 1,1 '-carbonyl-diimidazole (197 mg, 1.21 mmol) and DMF (7 ml) was stirred at 50° C. for 1 h. After cooling to r.t., 1-(2-methylamino-ethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (335 mg, 1.27 mmol) was added and stirring was continued for 1 h. After the addition of water, the mixture was extracted with ether. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica gel, dichloromethane-methanol 95:5) to give 4-benzyloxy-N-[2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-ethyl]-N-methyl-benzamide (226 mg) as a pale yellow oil. MS: me/e=473 (M+H)+.

Workup

temperatureAfter cooling to r.t.
stirringstirring
waitwas continued for 1 h
extractionthe mixture was extracted with ether
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
customevaporated
customThe residue was purified by chromatography (silica gel, dichloromethane-methanol 95:5)

Sources & evidence

ORD record: ord-807c3e257e8a48448a0f93892b995449
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05889026

Reaction notes

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