Benzoyl chloride → N-(5,6-Diethyl-indan-2-yl)-benzamide

HRID 244777Notes

Reaction equation

HRID 244777 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH2:14])[CH2:6]2)[CH3:2].C(N(CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[CH2:12]([C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[CH2:1][CH3:2])[CH2:6][CH:7]([NH:14][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:8]2)[CH3:13]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 101926155,6-diethyl-2,3-dihydro-1H-inden-2-amine

Product 1

HCID 22499179N-(5,6-Diethyl-indan-2-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6-Diethyl-indan-2-ylamine (4.10 g) is dissolved in dichloromethane (DCM) (150 mL) and triethylamine (2.41 g) is added. Benzoyl chloride (3.20 g) is then added dropwise and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by TLC after 1 hour. The solution is washed with 0.2M HCl (100 mL), water (100 mL) and brine (100 mL). The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. Crystallised from ethyl acetate. TLC (silica, dichloromethane/methanol 10:1 Rf=0.85).

Workup

  1. washThe solution is washed with 0.2M HCl (100 mL), water (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. customCrystallised from ethyl acetate

Sources & evidence

ORD record
ord-d6637ed056bf4cdeaba1de49ab8cd62a
Source dataset
uspto-grants-2014_02
Patent number
US08658673B2

Reaction notes

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