4-(Phenoxymethyl)piperidine → 2-Amino-1-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-3-nitrobenzene

HRID 614834Notes

Reaction equation

HRID 614834 reaction equation
[NH2:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[O:8][CH2:7]1.[O:16]([CH2:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[NH2:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]([OH:8])[CH2:7][N:27]1[CH2:28][CH2:29][CH:24]([CH2:23][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 30174444-(Phenoxymethyl)piperidineHCID 113448381-(2-Amino-3-nitrophenoxy)-2,3-epoxypropane

Product 1

HCID 213273122-Amino-1-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 40.0 g. 1-(2-amino-3-nitrophenoxy)-2,3-epoxypropane, 36.2 g. 4-phenoxymethylpiperidine and 450 ml. ethanol is stirred for 18 hours at ambient temperature and the solution thereby obtained of 2-amino-1-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-3-nitrobenzene (m.p. 117°-118° C.) is subsequently hydrogenated at ambient temperature in the presence of 1.0 g. platinum oxide. After filtration, the filtrate obtained is acidified with dilute hydrochloric acid, evaporated and the evaporation residue redissolved in ethanol/ethyl acetate. There are obtained 72.3 g. 2,3-diamino-1-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-benzene trihydrochloride (81% of theory) in the form of an amorphous substance.

Workup

  1. additionA mixture of 40.0 g

Sources & evidence

ORD record
ord-1c919157d63b4789acda1d6d8b1b2d84
Source dataset
uspto-grants-1979_03
Patent number
US04146630

Reaction notes

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