4-Nitrobenzoyl chloride → HCID 18621504, compound

HRID 1861754Notes

Reaction equation

HRID 1861754 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][NH2:21])=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>C(Cl)Cl.CCN(CC)CC>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][NH:21][C:29](=[O:30])[C:28]2[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:33][CH:32]=2)=[O:19])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 18621443HCID 18621443, compound

Product 1

HCID 18621504HCID 18621504, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 5-(4-benzylpiperidin-1-yl)valerhydrazide (289 mg, 1.00 mmol) in 10 mL of CH2Cl2 and 0.21 mL of Et3N was added 4-nitrobenzoyl chloride (278 mg, 1.50 mmol). The resulting solution was allowed to stir at rt for 12 hr. The mixture was poured into ice water (10 g). The organic layer was separated and the water phase was extracted with CH2Cl2 (2×15 mL). The combined organic extracts were dried over Na2SO4. Evaporation of solvent gave the title product as a brown oil (405 mg, 92%): 1H NMR (CDCl3) 1.25 (m, 2 H), 1.60 (m, 6 H), 1.90 (m, 2 H), 2.29 (m, 4 H), 2.48 (d, J=6.6 Hz, 2 H), 2.90 (m, 2 H), 3.42 (s, 1 H), 7.07-7.24 (m 5 H), 7.70 (bs, 2 H), 7.96 (d, J=7.8 Hz, 2 H), 8.08 (d, J=7.8 Hz, 2 H).

Workup

  1. customThe organic layer was separated
  2. extractionthe water phase was extracted with CH2Cl2 (2×15 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-a003352558294ab7be6a227edb49483c
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

Loading…