5,6,7,8-Tetrahydro-2-naphthylamine → HCID 69673496, compound

HRID 2276332Notes

Reaction equation

HRID 2276332 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[NH2:11].[C:12]([CH:15]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:16]([O:18][CH3:19])=[O:17])(=O)[CH3:13]>>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[C:15]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:16]([O:18][CH3:19])=[O:17])[CH3:13]

Participants

3

Reactant 2

HCID 751935,6,7,8-Tetrahydro-2-naphthylamineHCID 112039Dimethyl acetylsuccinate

Product 1

HCID 69673496HCID 69673496, compoundYield 65.6%

Procedure

The 5,6,7,8-tetrahydronaphthalen-2-amine (10 g; 68 mmol) and dimethyl acetylsuccinate (11.6 g; 62 mmol) were mixed together, placed in a dessicator and the homogeneous mixture was stirred under vacuum (3 mbars) for 3 days. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (1 to 20%) in heptane furnished 12.9 g (60%) of dimethyl 2-(1-(5,6,7,8-tetrahydronaphthalen-2-ylamino)ethylidene)succinate as a deep orange oil.

Workup

  1. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (1 to 20%) in heptane

Sources & evidence

ORD record
ord-c7f861ee487e4489b235176b2590e9c4
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

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