Hydrochloric Acid → (4-Fluorophenyl)(3-hydroxypiperidin-1-yl)methanone

HRID 1696821Notes

Reaction equation

HRID 1696821 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[F:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C.Cl>ClCCl>[F:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:4]2[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]2)=[O:14])=[CH:11][CH:10]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 232933-HydroxypiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 45786480(4-Fluorophenyl)(3-hydroxypiperidin-1-yl)methanoneYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-hydroxypiperidine (0.6 g, 5.93 mmol), 4-fluorobenzoic acid (0.83 g, 5.93 mmol), HOBT (0.8 g, 5.93 mmol), EDCI.HCl (1.7 g, 8.9 mmol) and dry triethylamine (1.66 mL, 11.86 mmol) in dry dichloromethane (30 mL) was kept under stiffing overnight at ambient temperature, under nitrogen atmosphere. HCl 1N (30 mL) was then added and the phases separated. The organic layer was washed with HCl 1N (30 mL), with NaOH 1N (30 mL×2 times), then with water (30 mL). Evaporation of the organic solvent afforded (4-fluoro-phenyl)-(3-hydroxy-piperidin-1-yl)-methanone as a white oil (0.7 g).

Workup

  1. customthe phases separated
  2. washThe organic layer was washed with HCl 1N (30 mL), with NaOH 1N (30 mL×2 times)
  3. customEvaporation of the organic solvent

Sources & evidence

ORD record
ord-a0d7a6b4dda649ce8dc6a5920f0c4a96
Source dataset
uspto-grants-2012_04
Patent number
US08163775B2

Reaction notes

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