Dimethyl Sulfoxide → 4-[4-[4-(Hydoxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-alpha,alpha-dimethylbenzeneacetaldehyde

HRID 266397Notes

Reaction equation

HRID 266397 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].CS(C)=O.[OH:11][C:12]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([C:24]2[CH:32]=[CH:31][CH:27]([CH2:28]CO)[C:26]([CH3:34])([CH3:33])[CH:25]=2)=[O:23])[CH2:15][CH2:14]1.OOS([O-])=O.[K+]>C(Cl)Cl.O.C(N(CC)CC)C>[OH:11][C:12]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH2:21][C:22]([C:24]2[CH:32]=[CH:31][C:27]([C:26]([CH3:33])([CH3:34])[CH:2]=[O:3])=[CH:28][CH:25]=2)=[O:23])[CH2:17][CH2:18]1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 23707502Potassium hydroxy sulfiteHCID 701480474-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl alcohol

Product 1

HCID 110599524-[4-[4-(Hydoxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-alpha,alpha-dimethylbenzeneacetaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×HCID 8471TriethylamineSolvent

Conditions

Temperature
-55 °C

Procedure

Dissolve oxalyl chloride (1.57 g, 12.4 mmol) in methylene chloride (17 mL), cool to -55° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution of dimethylsulfoxide (1.77 g, 1.61 mL) in methylene chloride (4.5 mL). Stir for 15 minutes and add, by dropwise addition, a solution of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl alcohol (5.0 g, 10.3 mol) in methylene chloride (33 mL). Stir for 30 minutes and add, by dropwise addition, triethylamine (7.2 mL). Stir for 15 minutes and then allow to warm to -10° C. Add a solution of oxone (12.66 g) in deionized water (50 mL). Stir for 15 minutes and add methylene chloride (25 mL). Separate the organic phase, wash with brine, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (ethyl acetate) to give 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetaldehyde.

Workup

  1. additionAdd, by dropwise addition
  2. additionadd, by dropwise addition
  3. stirringStir for 30 minutes
  4. stirringStir for 15 minutes
  5. temperatureto warm to -10° C
  6. stirringStir for 15 minutes
  7. customSeparate the organic phase
  8. washwash with brine
  9. dry with materialdry (MgSO4)
  10. customevaporate the solvent in vacuo
  11. customPurify by chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5689434f97f446279c477eba8776887e
Source dataset
uspto-grants-1997_07
Patent number
US05650516

Reaction notes

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