Triethylamine → HCID 86215693, compound

HRID 1760832Notes

Reaction equation

HRID 1760832 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH2:14])[CH:5]=[CH:4][C:3]1=2.C(N(CC)CC)C.[C:23](Cl)(=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>ClCCl>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH:14][C:23](=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 114697605,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine

Product 1

HCID 86215693HCID 86215693, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamine (1) (0.5 g, 2.46 mmole) in 20 mL of dichloromethane was treated successively with 0.51 mL of triethylamine (1.5 eq.) and 0.35 mL of hexanoyl chloride (1 eq.). The reaction mixture was stirred at room temperature for two hours, diluted with an additional 20 mL of dichloromethane and washed with two 50 mL portions of water and one 50 mL portion of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo, giving 740 mg (100%) of hexanoic acid (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amide (15) as a pale yellow oil.

Workup

  1. washwashed with two 50 mL portions of water and one 50 mL portion of saturated aqueous sodium chloride solution
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ee5f40e90c44757994cc480639d61af
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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