Chloride → HCID 10513182, compound

HRID 890352Notes

Reaction equation

HRID 890352 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-bc83e1e022cb49489ba702974a3067a3
Source dataset
uspto-grants-2006_02
Patent number
US06995268B2

Reaction notes

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