4-Nitrobenzoyl chloride → HCID 66878228, compound

HRID 1878323Notes

Reaction equation

HRID 1878323 reaction equation
Cl.Cl.[C:3]([NH:7][C:8](=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:10]=1)([CH3:6])([CH3:5])[CH3:4].C(N(C(C)C)C(C)C)C.[N+:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1)([O-:34])=[O:33]>ClCCl>[C:3]([NH:7][C:8](=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]2[CH2:17][CH2:18][N:19]([C:39](=[O:40])[C:38]3[CH:37]=[CH:36][C:35]([N+:32]([O-:34])=[O:33])=[CH:43][CH:42]=3)[CH2:20][CH2:21]2)[CH:10]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 66878161HCID 66878161, compound

Product 1

HCID 66878228HCID 66878228, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-tert-Butyl-3-(piperazin-1-ylmethyl)benzamide dihydrochloride (0.50 g, 1.44 mmol) was suspended in stirred dichloromethane (20 mL) at 0° C. (ice-bath) under an argon atmosphere. N-ethyl-N-isopropylpropan-2-amine (1.0 mL, 5.75 mmol) was added slowly. After 10 minutes stirring, the resulting solution was treated with a suspension of 4-nitrobenzoyl chloride (0.267 g, 1.44 mmol) In dichloromethane (10 ml). The ice-bath was removed and stirring continued for 1 hour. The solution was diluted with dichloromethane (70 mL) and washed with water (×4). The organic phase was dried on magnesium sulfate, filtered and concentrated under vacuum to give the title compound (0.58 g) as a yellow foam.

Workup

  1. customThe ice-bath was removed
  2. stirringstirring
  3. waitcontinued for 1 hour
  4. additionThe solution was diluted with dichloromethane (70 mL)
  5. washwashed with water (×4)
  6. customThe organic phase was dried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dcc8ad27f44b450a80329b173a93e552
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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