Methyl Isocyanate → 2-Dipropylamino-8-[2-(3-methylureido)ethyl]-1,2,3,4-tetrahydronaphthalene

HRID 728090Notes

Reaction equation

HRID 728090 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][CH2:16][NH2:17])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[CH3:21][N:22]=[C:23]=[O:24]>C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][CH2:16][NH:17][C:23]([NH:22][CH3:21])=[O:24])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 141812202-Dipropylamino-8-(2-aminoethyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 141812242-Dipropylamino-8-[2-(3-methylureido)ethyl]-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 1140TolueneSolvent

Procedure

1.3 g (4.7 mmol) of 2-dipropylamino-8-(2-aminoethyl)-1,2,3,4-tetrahydronaphthalene were initially introduced into 20 ml of toluene. The reaction was catalyzed using 3 drops of triethylamine, and 0.31 ml (5.17 mmol) of methyl isocyanate were then added dropwise. The mixture was stirred overnight at room temperature, and then evaporated. After subsequent chromatography over silica gel 60, 40-63 μm, using diisopropyl ether/ethanol/triethylamine, the product was stirred with petroleum ether and a little diisopropyl ether, and filtered off under suction.

Workup

  1. additionwere then added dropwise
  2. customevaporated
  3. stirringthe product was stirred with petroleum ether
  4. filtrationa little diisopropyl ether, and filtered off under suction

Sources & evidence

ORD record
ord-961e3d617f6f41be927efff9ab44b63f
Source dataset
uspto-grants-1991_09
Patent number
US05047422

Reaction notes

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