Ethanol → 4-[Acetyl-(4-{2-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenyl)-amino]-piperidine-1-carboxylic acid octylamide

HRID 395985Notes

Reaction equation

HRID 395985 reaction equation
C([O:8][C:9]1[CH:46]=[CH:45][C:12]([O:13][CH2:14][C@@H:15]([OH:44])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:43]=[CH:42][C:23]([NH:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:32])[CH2:27][CH2:26]3)=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H].[CH2:49]([OH:51])[CH3:50]>[Pd]>[CH2:34]([NH:33][C:31]([N:28]1[CH2:27][CH2:26][CH:25]([N:24]([C:49](=[O:51])[CH3:50])[C:23]2[CH:42]=[CH:43][C:20]([CH2:19][CH2:18][NH:17][CH2:16][C@H:15]([OH:44])[CH2:14][O:13][C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:46][CH:45]=3)=[CH:21][CH:22]=2)[CH2:30][CH2:29]1)=[O:32])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 3

HCID 702EthanolHCID 699867294-{4-[2-({(2S)-3-[4-(Benzyloxy)phenoxy]-2-hydroxypropyl}amino)-ethyl]anilino}-N-octyl-1-piperidinecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 101210514-[Acetyl-(4-{2-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenyl)-amino]-piperidine-1-carboxylic acid octylamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-{4-[2-({(2S)-3-[4-(Benzyloxy)phenoxy]-2-hydroxypropyl}amino)-ethyl]anilino}-N-octyl-1-piperidinecarboxamide (0.1 g, 0.15 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.1 g) added. The mixture was shaken on a Parr apparatus overnight under 50 psi hydrogen. The mixture was cooled to ambient temperature, filtered through a Celite pad, and the solvent removed in vacuo to yield the title compound (eluant: 5:1 chloroform-methanol) (0.033 g, 0.05 mmol)

Workup

  1. filtrationfiltered through a Celite pad
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c8640c3228f040abbb3b123b478ba953
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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