2-Amino-7-carbethoxymethoxytetraline hydrochloride → Styrene Oxide

HRID 467316Notes

Reaction equation

HRID 467316 reaction equation
[H][H].Cl.[NH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:11]=2)[CH2:6]1>>[C:7]1([CH:8]2[CH2:9][O:15]2)[CH:12]=[CH:13][CH:14]=[CH:5][CH:6]=1.[NH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:11]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 200947462-Amino-7-carbethoxymethoxytetraline hydrochlorideHCID 178418361HCID 178418361, compound

Product 2

HCID 7276Styrene OxideHCID 112996642-Amino-7-carbethoxymethoxytetraline

Procedure

A solution of 27 g of 2-benzylamino-7-carbethoxymethoxytetraline hydrochloride, EXAMPLE 1, in 300 ml of 95% ethanol and 25 ml of water, is hydrogenated under ordinary pressure and at temperature of 50° C. by using 3 g of 10% palladium on charcoal as a catalyst. After 3 hours, the mixture is filtered, the residue is taken up twice with 100 ml of absolute ethanol and dried every time. The product so obtained is triturated in 150 ml of acetone, filtered and crystallized from 100 ml of isopropanol to give 19 g of 2-amino-7-carbethoxymethoxytetraline hydrochloride; m.p. 143°-145° C. The product thus obtained may be used for the preparation of the compound of formula (XV) above, in which X is hydrogen and O-R' is a carbethoxymethoxy group (COMPOUND 1), as follows: A solution of 1.8 g of phenyloxirane and 3.7 g of 2-amino-7-carbethoxymethoxytetraline base, obtained by neutralization of the hydrochloride described above, in 40 ml of n-butanol is heated under reflux for 6 hours. The mixture is concentrated to dryness, the residue is purified by flash chromatography, by eluting with a mixture of ethyl acetate/methanol 9/1. The purified oil is left to react overnight with an excess of oxalic acid in 5 ml of isopropanol. Thus, 1.9 g of N-(7-carbethoxymethoxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-2-phenylethanamine oxalate is obtained; m.p. 159°-162° C., identical with the compound of Example 5 of the European patent 211 721.

Workup

  1. customThe product thus obtained may

Sources & evidence

ORD record
ord-9265c76e566b4ddd906abf57cdd22523
Source dataset
uspto-grants-1992_10
Patent number
US05159103

Reaction notes

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