1-{benzyl[2-(2-methoxyphenoxy)ethyl]amino}-3-(9H-carbazol-4-yloxy)propan-2-ol → Carvedilol

HRID 1836719Notes

Reaction equation

C([N:8]([CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])[CH2:9][CH:10]([OH:26])[CH2:11][O:12][C:13]1[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[CH:16]1[C:17]2[NH:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]=2[C:13]([O:12][CH2:11][CH:10]([OH:26])[CH2:9][NH:8][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH3:37])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

10 g of 1-{Benzyl-[2-(2-methoxy-phenoxy)-ethyl]-amino}-3-(9H-carbazol-4-yloxy)-propan-2-ol (20 mmol) were dissolved in 80 ml methanol. 1 g of Pd—C (10%) were added and the suspension was warmed to 50° C. The mixture was hydrogenated at normal pressure for about 7 hours. The Pd-catalyst was filtered under suction and washed with 25 ml of hot methanol. 80 ml of methanol were distilled off and the residue was cooled to 0° C. and hold at this temperature for 6 h. The product was filtered and washed twice with 3 ml cold methanol. The substance was dried at 60° C. for 12 h.

Workup

filtrationThe Pd-catalyst was filtered under suction
washwashed with 25 ml of hot methanol
distillation80 ml of methanol were distilled off
temperaturethe residue was cooled to 0° C.
waithold at this temperature for 6 h
filtrationThe product was filtered
washwashed twice with 3 ml cold methanol
customThe substance was dried at 60° C. for 12 h.

Sources & evidence

ORD record: ord-edd35f7e303d426cb89931cd49461db0
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777559B2

Reaction notes

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