N-[2-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-2-hydroxyethyl]-N-benzyloxycarbonyl-6-(4-phenylbutoxy)hexylamine → 1-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-2-(6-(4-phenylbutoxy)hexylamino)ethanol

HRID 1936218Notes

Reaction equation

HRID 1936218 reaction equation
[CH3:1][C:2]1([CH3:43])[O:7][CH2:6][C:5]2[CH:8]=[C:9]([CH:12]([OH:42])[CH2:13][N:14]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)C(OCC3C=CC=CC=3)=O)[CH:10]=[CH:11][C:4]=2[O:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:43])[O:7][CH2:6][C:5]2[CH:8]=[C:9]([CH:12]([OH:42])[CH2:13][NH:14][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:10]=[CH:11][C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 11467416N-[2-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-2-hydroxyethyl]-N-benzyloxycarbonyl-6-(4-phenylbutoxy)hexylamine

Product 1

HCID 101827471-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-2-(6-(4-phenylbutoxy)hexylamino)ethanolYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.9 g (1.53 mmol) N-[2-(2,2-dimethyl-4H-benzo[1,3]-dioxin-6-yl)-2-hydroxyethyl]-N-benzyloxycarbonyl-6-(4-phenylbutoxy)hexylamine is hydrogenated with 0.1 g 5% Pd/C in 30 ml MeOH at atmospheric pressure and room temperature. Once 50 ml H2 have been absorbed, the catalyst is filtered off on decalite and the filtrate concentrated to dryness to give 0.69 g (99%) N-[2-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-2-hydroxyethyl]-6-(4-phenylbutoxy)hexylamine.

Workup

  1. customOnce 50 ml H2 have been absorbed
  2. filtrationthe catalyst is filtered off on decalite
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-e76676060713450eb364528bdf17e917
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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