2-[N-Methyl-N-(2-cyano-ethyl)-amino]-7-methoxy-1,2,3,4-tetrahydronaphthalene → 1-Amino-3-[N-methyl-N-(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

HRID 1380868Notes

Reaction equation

HRID 1380868 reaction equation
[CH3:1][N:2]([CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)[CH2:8]1)[CH2:3][CH2:4][C:5]#[N:6]>CO.N.[Ni]>[NH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)[CH2:8]1

Participants

5

Reactant 1

HCID 233245732-[N-Methyl-N-(2-cyano-ethyl)-amino]-7-methoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 233245881-Amino-3-[N-methyl-N-(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

First, 2-[N-methyl-N-(2-cyano-ethyl)-amino]-7-methoxy-1,2,3,4-tetrahydronaphthalene (6.7 g, 0.0274 mol) is dissolved in methanol (80 ml) saturated with ammonia at 20° C., then Raney nickel (0.8 g) is added and the mixture is hydrogenated at 50° C. under hydrogen pressure (5 bar) for 3 hours. The catalyst is filtered off and the filtrate is evaporated by rotary evaporation. Yield: 5.4 g. Rf value: 0.25 (alumina, eluant: 95 parts by volume of methylene chloride+5 parts by volume of ethanol).

Workup

  1. customis hydrogenated at 50° C. under hydrogen
  2. customfor 3 hours
  3. filtrationThe catalyst is filtered off
  4. customthe filtrate is evaporated by rotary evaporation

Sources & evidence

ORD record
ord-6237bbdb9b2d4c03a55397ac70d76e02
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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