5,6-Dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine → HCID 20058477, compound

HRID 2050567Notes

Reaction equation

HRID 2050567 reaction equation
[O:1]=[C:2]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:31][O:32][C:33]1[C:42]([O:43][CH3:44])=[CH:41][CH:40]=[C:39]2[C:34]=1[CH2:35][CH2:36][CH:37]([NH2:45])[CH2:38]2>ClCCl>[CH3:31][O:32][C:33]1[C:42]([O:43][CH3:44])=[CH:41][CH:40]=[C:39]2[C:34]=1[CH2:35][CH2:36][CH:37]([NH:45][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][C:2]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:1])[CH2:38]2

Participants

5

Reactant 3

HCID 306575,6-Dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amineHCID 682631,1'-CarbonyldiimidazoleHCID 10777012HCID 10777012, compound

Product 1

HCID 20058477HCID 20058477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-oxo-6-(2-phenylethylamino)hexanoic acid (2.49 g) and carbonyldiimidazole (1.62 g) in dry dichloromethane (100 ml) was stirred under a nitrogen atmosphere for 2 hours at room temperature. A solution of 1,2,3,4-tetrahydro-5,6-dimethoxy-2- aminonaphthalene (2.07 g) in dichloromethane (20 ml) was added and the solution stirred at room temperature for 18 hours. The solution was washed with dilute hydrochloric acid, dilute sodium carbonate solution and water. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated to leave the sub-title compound which crystallised from isopropanol as colorless flakes (3.8 g), m.p. 191°-193°.

Workup

  1. washThe solution was washed with dilute hydrochloric acid, dilute sodium carbonate solution and water
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-449154492f514b4a86fe3726e686df54
Source dataset
uspto-grants-1991_05
Patent number
US05013760

Reaction notes

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