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

HRID 2401593Notes

Reaction equation

HRID 2401593 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-76150ae9ade446e291c5b8e0a4219b1f
Source dataset
uspto-grants-2014_08
Patent number
US08796307B2

Reaction notes

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