2-Fluorobenzonitrile → HCID 22615438, compound

HRID 842796Notes

Reaction equation

HRID 842796 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[OH:15].C(N(C(C)C)CC)(C)C>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[N:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[OH:15])#[N:5]

Participants

6

Reactant 3

HCID 678552-FluorobenzonitrileHCID 81531DiisopropylethylamineHCID 19601345HCID 19601345, compound

Product 1

HCID 22615438HCID 22615438, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 2-fluorobenzonitrile (4.03 g, 33.2 mmol) and pyrolidin-2-ol (2.92 g, 33.5 mmol) was treated with diisopropylethylamine (4.37 g, 33.8 mmol) at room temperature. The mixture was stirred at room temperature (5 d). The resulting mixture was diluted with dichloromethane and sodium carbonate solution and the aqueous layer was extracted with two additional portions of dichloromethane. The combined organic extracts were washed with brine and dried over Na2SO4. The solvent was removed in vacuo. PCTLC (SiO2, 6 mm, 20% EtOAc-80% hexane) afforded the title compound (57).

Workup

  1. extractionthe aqueous layer was extracted with two additional portions of dichloromethane
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ee7b9f02cb404d32837aafc6cc493d3c
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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