Chloride → HCID 10513182, compound

HRID 736360Notes

Reaction equation

HRID 736360 reaction equation
[Cl-].CS(C)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][CH2:15]2)=[CH:9][CH:8]=1.CCN(CC)CC>C(Cl)Cl.O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH:20]=[O:21])[CH2:16][CH2:15]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 312Chloride2×HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 10489280[1-(4-fluorobenzyl)piperidin-4-yl]methanol

Product 1

HCID 10513182HCID 10513182, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxylyl chloride (0.59 ml, 3.95 mmol) in CH2Cl2 (20 ml) was cooled to −78° C. DMSO (0.95 ml, 13.38 mmol) was added dropwise into the oxylyl chloride solution. The reaction mixture was stirred for 5 minutes, and 1-[(4-fluorophenyl)methyl]-4-piperidinemethanol (0.99 g, 4.46 mmol) in CH2Cl2 (20 ml) was added dropwise into the reaction solution. Stirring was continued for an additional 20 minutes. Et3N, 8.0 ml was added and the reaction mixture was stirred for 10 minutes and then allowed to warm to room temperature. Water (50 ml) was added and the mixture was extracted with CH2Cl2. The combined CH2Cl2 solution was dried over Na2SO4. The evaporation of solvent gave an oil, 0.77 g (79% yield). 1H NMR (CD3Cl) δ 9.65 (1H, s, CHO), 7.30-7.24 (2H, m, Ar—H), 7.00-6.97 (2H, m, Ar—H), 3.46 (2H, s, p-FPhCH2), 2.81-2.76 (2H, m, N(CH)2), 2.30-2.20 (1H, m, CHCHO), 2.14-2.06 (2H, dt, J=2.1, 11.3 Hz, N(CH)2), 1.92-1.86 (2H, dd, J=3.5, 13.5 Hz), 1.74-1.62 (2H, m).

Workup

  1. stirringStirring
  2. waitwas continued for an additional 20 minutes
  3. stirringthe reaction mixture was stirred for 10 minutes
  4. extractionthe mixture was extracted with CH2Cl2
  5. dry with materialThe combined CH2Cl2 solution was dried over Na2SO4
  6. customThe evaporation of solvent
  7. customgave an oil, 0.77 g (79% yield)

Sources & evidence

ORD record
ord-bfef24c478e9454ba92b11d30c46980b
Source dataset
uspto-grants-2009_09
Patent number
US07595331B2

Reaction notes

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