(2S)-2-[(2-allylphenoxy)methyl]oxirane → 4-(4-{2-[(2S)-3-(2-Allyl-phenoxy)-2-hydroxy-propylamino]-ethyl}-phenylamino)-piperidine-carboxylic acid octylamide

HRID 395978Notes

Reaction equation

HRID 395978 reaction equation
C(O)=O.[NH2:4][CH2:5][CH2:6][C:7]1[CH:30]=[CH:29][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.[CH2:31]([C:34]1[CH:44]=[CH:43][CH:42]=[CH:41][C:35]=1[O:36][CH2:37][C@@H:38]1[CH2:40][O:39]1)[CH:32]=[CH2:33]>>[CH2:21]([NH:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][NH:4][CH2:40][C@H:38]([OH:39])[CH2:37][O:36][C:35]3[CH:41]=[CH:42][CH:43]=[CH:44][C:34]=3[CH2:31][CH:32]=[CH2:33])=[CH:30][CH:29]=2)[CH2:13][CH2:14]1)=[O:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 968915(2S)-2-[(2-allylphenoxy)methyl]oxiraneHCID 699872524-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 101444414-(4-{2-[(2S)-3-(2-Allyl-phenoxy)-2-hydroxy-propylamino]-ethyl}-phenylamino)-piperidine-carboxylic acid octylamideYield 14%

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate (0.40 g, 0.95 mmol) was reacted with (2S)-2-[(2-allylphenoxy)methyl]oxirane (0.125 g, 0.713 mmol) according to Procedure G to give the title compound (eluant: 20:1 chloroform-methanol) (0.060 g, 0.1 mmol).

Sources & evidence

ORD record
ord-b41d470825324e69b3f9fd479673be71
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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