Triethylamine → N-(1,3-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)-3,3-dimethylbutanamide

HRID 1662283Notes

Reaction equation

HRID 1662283 reaction equation
[NH2:1][C:2]1[C:3]([CH3:14])=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2.C(N(CC)CC)C.[C:22]([CH2:26][C:27](Cl)=[O:28])([CH3:25])([CH3:24])[CH3:23]>ClCCl>[CH3:14][C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][C:8](=[O:13])[C:9]=2[CH:10]=[C:11]([CH3:12])[C:2]=1[NH:1][C:27](=[O:28])[CH2:26][C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 552716636-Amino-5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 59808904N-(1,3-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)-3,3-dimethylbutanamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-amino-5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one (1 g, 5.3 mmol) and triethylamine (1.07 g, 10.6 mmol) in anhydrous dichloromethane (20 ml) was added dropwise tert-butylacetyl chloride (0.78 g, 5.8 mmol) at room temperature. The reaction mixture was stirred an additional 3 hours at this temperature. The solvent was removed under reduced pressure, and the residue was purified by Biotage (hexane/EtOAc, 0-40%, 40 min) to give a white solid (1.4 g, 92%). 1H-NMR δ (CDCl3, 300 MHz): 7.82 (s, 1H), 6.73 (brs, 1H, exchangeable with D2O), 2.85 (t, J=6.0 Hz, 2H), 2.60 (t, J=6.0 Hz, 2H), 2.33 (s, 2H), 2.27 (s, 3H), 2.18 (s, 3H), 2.15 (m, J=6.0 Hz, 2H), 1.16 (s, 9H). MS: 288 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by Biotage (hexane/EtOAc, 0-40%, 40 min)

Sources & evidence

ORD record
ord-d6d60b2894454ec09be266adfa0048c0
Source dataset
uspto-grants-2011_10
Patent number
US08030518B2

Reaction notes

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