4-Nitrobenzoyl chloride → HCID 18621504, compound

HRID 324531Notes

Reaction equation

HRID 324531 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-9b7d8aed0927420aa283f713614d7cba
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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