Diisopropylethylamine → 3,4-Dimethyl-7-[3-(4-oximino-piperidino)-propoxy]-coumarin

HRID 1065642Notes

Reaction equation

HRID 1065642 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH3:18])=[C:11]([CH3:17])[C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1.Cl.[N:20](=[C:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[OH:21].CCN(C(C)C)C(C)C>O1CCOCC1>[CH3:17][C:11]1[C:12](=[O:16])[O:13][C:14]2[C:9]([C:10]=1[CH3:18])=[CH:8][CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:25]1[CH2:26][CH2:27][C:22](=[N:20][OH:21])[CH2:23][CH2:24]1)[CH:15]=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 147153567-(3-Bromopropoxy)-3,4-dimethylcoumarinHCID 19106851N-(piperidin-4-ylidene)hydroxylamine hydrochloride

Product 1

HCID 204733543,4-Dimethyl-7-[3-(4-oximino-piperidino)-propoxy]-coumarin

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

By the reaction of 7-(3-bromopropoxy)-3,4-dimethylcoumarin with 4-oximino-piperidine hydrochloride in dioxane solution in the presence of a Hunig base, there is obtained 3,4-dimethyl-7-[3-(4-oximino-piperidino)-propoxy]-coumarin (m.p. 198°-200° C.), from which, by catalytic hydrogenation over Raney nickel in ammoniacal methanol, there is obtained 7-[3-(4-amino-piperidino)-propoxy]-3,4-dimethyl-coumarin; m.p. 92°-94° C.

Sources & evidence

ORD record
ord-64db9d85019345f9bf250fbf9b4ba1a2
Source dataset
uspto-grants-1982_05
Patent number
US04330549

Reaction notes

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