HCID 12510287, compound → 4-(1-Adamantyloxy)-2,6-dimethylaniline

HRID 2050220Notes

Reaction equation

HRID 2050220 reaction equation
[C:1]12([O:11][C:12]3[CH:18]=[C:17]([CH3:19])[C:15]([NH2:16])=[C:14]([CH2:20]SC)[CH:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>[Ni]>[C:1]12([O:11][C:12]3[CH:13]=[C:14]([CH3:20])[C:15]([NH2:16])=[C:17]([CH3:19])[CH:18]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

3

Reactant 1

HCID 12510287HCID 12510287, compound

Product 1

HCID 125102894-(1-Adamantyloxy)-2,6-dimethylanilineYield 29.6%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst2×

Procedure

9.6 g (33.6 mmoles) of 4-(1-adamantyloxy)-2-(methylthiomethyl)-6-methylaniline is disulfurized as in Example 89 using six rounded teaspoonfuls of Raney nickel sludge (approximately 48 g of Raney nickel). The product is chromatographed by HPLC on a 5.1 cm×109 cm column at 30 psi, eluting with CH2Cl2 followed by 0.5% acetone in CH2Cl2, 5 l., 0.75% acetone in CH2Cl2, 3 l., and 1% acetone in CH2Cl2, 5 l., affording 2.7 g of red solid. Center fractions (0.9 g) give product of m.p. 132.6-139.0.

Workup

  1. customThe product is chromatographed by HPLC on a 5.1 cm×109 cm column at 30 psi
  2. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-30a300e433ac4d81a92ce7c7e08e897c
Source dataset
uspto-grants-1980_04
Patent number
US04200588

Reaction notes

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