Hydrochloric Acid → HCID 51508031, compound

HRID 1172748Notes

Reaction equation

HRID 1172748 reaction equation
Cl.[F:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([NH:17][NH2:18])=[O:16])[CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C.Cl>ClCCl>[F:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([NH:17][NH:18][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([F:21])=[CH:23][CH:24]=3)=[O:16])[CH2:10]2)=[O:8])=[CH:5][CH:4]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666184083-Piperidinecarboxylic acid, 1-(4-fluorobenzoyl)-, hydrazide, hydrochloride (1:1), (3S)-

Product 1

HCID 51508031HCID 51508031, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-fluoro-benzoyl)-(S)-piperidine-3-carboxylic acid hydrazide hydrochloride, already prepared as described in Example 57 (C) (2.97 g, 11.2 mmol), 4-fluorobenzoic acid (1.68 g, 11.2 mmol), HOBT (1.5 g, 11.2 mmol), EDCI.HCl (3.2 g, 16.8 mmol) and dry triethylamine (5.43 mL, 39.5 mmol) in dry dichloromethane (80 mL) was kept under stirring overnight at ambient temperature, under nitrogen atmosphere. HCl 1N (80 mL) was then added and the phases separated. The organic layer was washed with HCl 1N (80 mL), with NaOH 1N (80 mL×2 times), then with water (80 mL). Evaporation of the organic solvent afforded a crude oil which was purified by flash chromatography (silica gel, eluent: DCM/MeOH/NH4OH 98/2/0.2). The compound obtained after column chromatography was purified again by flash chromatography (silica gel, eluent: DCM/MeOH/NH4OH 98/2/0.2) to provide the pure 4-fluoro-benzoic acid N′-[(S)-1-(4-fluoro-benzoyl)-piperidine-3-carbonyl]-hydrazide as a white solid (250 mg).

Workup

  1. customalready prepared
  2. customthe phases separated
  3. washThe organic layer was washed with HCl 1N (80 mL), with NaOH 1N (80 mL×2 times)
  4. customEvaporation of the organic solvent
  5. customafforded a crude oil which
  6. customwas purified by flash chromatography (silica gel, eluent: DCM/MeOH/NH4OH 98/2/0.2)
  7. customThe compound obtained after column chromatography
  8. customwas purified again by flash chromatography (silica gel, eluent: DCM/MeOH/NH4OH 98/2/0.2)

Sources & evidence

ORD record
ord-9a24265be5b14cf4ad7e76a3744c3dae
Source dataset
uspto-grants-2010_11
Patent number
US07834035B2

Reaction notes

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