Benzocaine → N-(4-carbethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-aminoethanol

HRID 346285Notes

Reaction equation

HRID 346285 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]3[CH2:16][O:15]3)[CH:5]=[CH:4][C:3]1=2.[NH2:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:23]([C:22]1[CH:21]=[CH:20][C:19]([NH:18][CH2:16][CH:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=3[CH:7]=2)[OH:15])=[CH:29][CH:28]=1)([O:25][CH2:26][CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 14726539(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)oxirane

Product 1

HCID 14726540N-(4-carbethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-aminoethanolYield 30.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

26 g (110 millimoles) of (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-oxirane, 15 g (90 millimoles) of ethyl 4-aminobenzoate, 135 g of basic alumina and 450 ml of toluene were refluxed for 2 hours. The solid was then filtered off and the filtrate was evaporated down. After recrystallization from n-heptane with a little ethyl acetate, the residue gave 11.0 g of N-(4-carbethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-aminoethanol. The structure was determined by H-NMR spectroscopy. 3-(4-Carbethoxyphenyl)-5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-oxazolidine:

Workup

  1. filtrationThe solid was then filtered off
  2. customthe filtrate was evaporated down
  3. customAfter recrystallization from n-heptane with a little ethyl acetate

Sources & evidence

ORD record
ord-828cf23b3459402eb9332ebcb1d2b72c
Source dataset
uspto-grants-1991_10
Patent number
US05061705

Reaction notes

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