Triethylamine → 5-Oxo-5-(4-phenylpiperazin-1-yl)pentanal

HRID 1942406Notes

Reaction equation

HRID 1942406 reaction equation
C(Cl)(=O)C(Cl)=O.[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13].C(N(CC)CC)C>ClCCl.CS(C)=O.[Cl-].[Na+].O>[O:13]=[C:12]([N:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:18][CH2:19]1)[CH2:11][CH2:10][CH2:9][CH:8]=[O:7]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 669376015-Hydroxy-1-(4-phenylpiperazin-1-yl)pentan-1-one

Product 1

HCID 866513155-Oxo-5-(4-phenylpiperazin-1-yl)pentanal

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 1.11 mL (12.8 mmol) oxalyl chloride in 35 mL of dichloromethane is cooled to −80° C. under argon atmosphere. 2.33 mL (32.7 mmol) of dimethylsulfoxide in 9.33 mL of dichloromethane is introduced dropwise over 10 minutes. After 5 minutes a solution of 1.84 (7 mmol) 5-hydroxy-1-(4-phenylpiperazin-1-yl)pentan-1-one in 8 mL dichloromethane and 2 mL dimethylsulfoxide is added over the course of 10 minutes. The reaction mixture is stirred for another hour at −80° C. before 5 mL of triethylamine is added and the mixture is allowed to warm up to room temperature. 50 mL of saturated brine solution is added for hydrolysis. The organic phase is separated, extracted three times with a saturated solution of sodium chloride, dried over sodium sulfate and the solvent is evaporated. The crude product is obtained in almost quantitative yield.

Workup

  1. additionis added
  2. customThe organic phase is separated
  3. extractionextracted three times with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-d48f935d23634ba298dd4290c79c7b38
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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