1,2,3,4-Tetrahydro-1-naphthylamine → HCID 69062509, compound

HRID 2221351Notes

Reaction equation

HRID 2221351 reaction equation
[CH3:1][C:2]1([CH3:16])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][C:13]([OH:15])=O)[CH:8]=2)[O:3]1.[CH:17]1([NH2:27])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1>C1COCC1>[CH3:16][C:2]1([CH3:1])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][C:13]([NH:27][CH:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH2:18]3)=[O:15])[CH:8]=2)[O:3]1

Participants

4

Reactant 2

HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 49757578(2,2-Dimethyl-2H-1-benzopyran-6-yl)acetic acid

Product 1

HCID 69062509HCID 69062509, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

9.6 g 1,1-carbonyldiimidazole (=CDl) dissolved in 85 ml THF was slowly added to a solution of 11.7 g of the 2,2-dimethyl-2H-chromen-6-yl acetic acid obtained above in 100 ml THF and stirred for 30 min. at room temperature. 8.8 ml 1,2,3,4-tetrahydro-1-naphthylamine, dissolved in 30 ml THF, was dropped slowly into this receiving solution, the resulting mixture was stirred for 1 hour and left to stand overnight at room temperature. The solvent was largely evaporated at reduced pressure, and the remaining residue was stirred with a mixture of diethyl ether and isopropanol (100:1 v/v) and crystallized. The resulting crystals were removed by suction and dried at 65° C. and 20 bar. Chromatography of the diethyl ether/isopropanol washing liquid on silica gel yielded further intermediate product, which was combined with the main quantity and dried. 17.5 g 2-(2,2-dimethyl-2H-chromen-6-yl)-N-1,2,3,4-tetrahydronaphth-1-yl acetamide was obtained as colorless solid, which was used without further purification for the subsequent reaction.

Workup

  1. additionwas dropped slowly into this receiving solution
  2. stirringthe resulting mixture was stirred for 1 hour
  3. waitleft
  4. waitto stand overnight at room temperature
  5. customThe solvent was largely evaporated at reduced pressure
  6. stirringthe remaining residue was stirred with a mixture of diethyl ether and isopropanol (100:1 v/v)
  7. customcrystallized
  8. customThe resulting crystals were removed by suction
  9. customdried at 65° C.
  10. customChromatography of the diethyl ether/isopropanol washing liquid on silica gel yielded further intermediate product, which
  11. customdried

Sources & evidence

ORD record
ord-6b1c560c4ad449f7bbb8ed3aa340319f
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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