Benzoyl chloride → HCID 19756255, compound

HRID 1587717Notes

Reaction equation

HRID 1587717 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2([CH2:25][NH2:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:12]1.C(N(CC)CC)C>C(OCC)C>[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2([CH2:25][NH:26][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:12]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10633128HCID 10633128, compound

Product 1

HCID 19756255HCID 19756255, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

The reaction is performed under a dry nitrogen atmosphere. 9.8 g (0.07 mol) of benzoyl chloride dissolved in 70 cm3 of diethyl ether are added dropwise to a solution of 16 g (0.07 mol) of 1-(1-methyl-3-indolyl)-cyclopentylmethylamine and 7.08 g (0.07 mol) of triethylamine in 70 cm3 of diethyl ether so as to maintain a gentle reflux of the ether, and the mixture is then stirred for 2 hours at room temperature. The precipitate formed is thereafter drained, the ether solution is washed with water, dried over sodium sulphate and filtered and the ether is evaporated off from the filtrate. The residue thereby obtained is crystallised by washing with cold diisopropyl ether.

Workup

  1. temperatureto maintain
  2. customThe precipitate formed
  3. washthe ether solution is washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe ether is evaporated off from the filtrate
  7. customThe residue thereby obtained
  8. customis crystallised
  9. washby washing with cold diisopropyl ether

Sources & evidence

ORD record
ord-db978277887a4ea08238de00d870526d
Source dataset
uspto-grants-1993_06
Patent number
US05219859

Reaction notes

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