Phosphorus oxychloride → HCID 12988956, compound

HRID 2220083Notes

Reaction equation

HRID 2220083 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([NH2:15])=O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].O=P(Cl)(Cl)Cl>CN(C=O)C.O>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]#[N:15])[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 129889553-(1-Propyl-4-piperidinyl)benzamide

Product 1

HCID 12988956HCID 12988956, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(1-propyl-piperidin-4-yl)-benzamide (350 mg) and POCl3 (326 μL) in dry DMF (6 ml) was heated at 80° C. for 3 h under an argon atmosphere. Evaporation of the solvent yielded a dark, oily residue, which was dissolved in water. The solution was basified and extracted with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. The oily residue was chromathographed on a silica column with MeOH:CH2Cl2 (1:19 (v/v)) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded pure 3-(1-Propyl-piperidin-4-yl)-benzonitrile (127 mg). The amine was converted into the fumarate salt and recrystallized from ethanol/diethylether: m.p. 122° C.; MS m/z (relative intensity, 70 eV) 228 (M+, 2), 199 (42), 129 (26), 70 (bp) 56 (53).

Workup

  1. customEvaporation of the solvent
  2. customyielded a dark, oily residue, which
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customCollection of the fractions
  8. additioncontaining pure
  9. customproduct and evaporation of the solvent

Sources & evidence

ORD record
ord-f4cff310f5934c57a66d9894b11ed40a
Source dataset
uspto-grants-2008_08
Patent number
US07417043B2

Reaction notes

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