5-Amino-6-(2,3-epoxypropoxy)-4-nitroindane → 5-amino-6-{3-[N-benzyl-2-(2-benzyloxyphenoxy)-ethylamino]-2-hydroxypropoxy}-4-nitroindane

HRID 67646Notes

Reaction equation

HRID 67646 reaction equation
[NH2:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH2:12][CH:13]1[O:15][CH2:14]1)[CH2:7][CH2:6][CH2:5]2.[CH2:19]([NH:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[NH2:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH2:12][CH:13]([OH:15])[CH2:14][N:26]([CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:7][CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 205133165-Amino-6-(2,3-epoxypropoxy)-4-nitroindaneHCID 20527498HCID 20527498, compound

Product 1

HCID 205275765-amino-6-{3-[N-benzyl-2-(2-benzyloxyphenoxy)-ethylamino]-2-hydroxypropoxy}-4-nitroindane

Procedure

The condensation of 5-amino-6-(2,3-epoxypropoxy)-4-nitroindane and N-benzyl-2-(2-benzyloxyphenoxy)-ethylamine gives 5-amino-6-{3-[N-benzyl-2-(2-benzyloxyphenoxy)-ethylamino]-2-hydroxypropoxy}-4-nitroindane in the form of an oil. This compound, in the form of its hydrochloride, is hydrogenated and hydrogenolytically debenzylated in methanolic solution in the presence of 10% palladium-charcoal to give 4,5-diamino-6-{2-hydroxy-3-[2-(2-hydroxyphenoxy)-ethylamino]-propoxy}-indane hydrochloride; m.p. 193°-195° C.

Sources & evidence

ORD record
ord-0be8c922cdcf4aa7ad18cc20061966c8
Source dataset
uspto-grants-1982_08
Patent number
US04346093

Reaction notes

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