Hexane → 4-[4-(2-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl)phenoxy}-N-octyl-1-piperidinecarboxamide

HRID 396027Notes

Reaction equation

HRID 396027 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:27]=[CH:26][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.C([O:35][C:36]1[CH:46]=[CH:45][C:39]([O:40][CH2:41][C@@H:42]2[CH2:44][O:43]2)=[CH:38][CH:37]=1)C1C=CC=CC=1.CCCCCC>ClCCl.CO>[OH:43][C@H:42]([CH2:41][O:40][C:39]1[CH:45]=[CH:46][C:36]([OH:35])=[CH:37][CH:38]=1)[CH2:44][NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:16])[CH2:11][CH2:10]2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 11817709(2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxiraneHCID 699879074-[4-(2-Aminoethyl)phenoxy]N-octyl-1-piperidinecarboxamide

Product 1

HCID 101872354-[4-(2-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl)phenoxy}-N-octyl-1-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

4-[4-(2-Aminoethyl)phenoxy]N-octyl-1-piperidinecarboxamide (0.825 g, 2.2 mmol) was reacted with (2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxirane (0.564 g, 2.2 mmol) according to Procedure G (eluant: 33:1 going to 9:1 dichloromethane-methanol) to give the title compound following crystallization from hexane (0.533 g, 0.84 mmol).

Workup

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Sources & evidence

ORD record
ord-dd460f9930c14be1919c389f306e88c6
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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