Dimethyl Sulfoxide → HCID 86591120, compound

HRID 1986961Notes

Reaction equation

HRID 1986961 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:35])([F:34])[C:13]1[CH:14]=[CH:15][C:16]2[C:20]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C@@H:28]4[CH2:30][C@H:29]4[CH2:31][OH:32])[CH2:23][CH2:22]3)=[CH:19][S:18][C:17]=2[CH:33]=1.C(N(CC)CC)C>C(Cl)Cl>[F:34][C:12]([F:11])([F:35])[C:13]1[CH:14]=[CH:15][C:16]2[C:20]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C@@H:28]4[CH2:30][C@H:29]4[CH:31]=[O:32])[CH2:23][CH2:22]3)=[CH:19][S:18][C:17]=2[CH:33]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68994515HCID 68994515, compound

Product 1

HCID 86591120HCID 86591120, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (62 μl, 0.72 mmol) in anhydrous methylene chloride (10 ml) under N2 was cooled to −78° C. while stirring. Dimethy sulfoxide (104 μl, 1.44 mmol) was then added followed by a solution of {(1R,2R)-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropyl}-methanol (0.135 g, .36 mmol) in anhydrous methylene chloride (10 ml). Stirring was continued at −78° for 35 minutes and then triethyl amine (1.0 ml, .7.3 mmol) was added. This solution was stirred for 4 hours and then removed from the cold bath, filtered, concentrated and chromatagraphed on silica gel with methylene chloride/methanol (95:5). The resultant pure aldehyde, (1R,2R)-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropanecarbaldehyde was verified by NMR and LC/MS, yielding 0.102 g, 76%.

Workup

  1. stirringStirring
  2. stirringThis solution was stirred for 4 hours
  3. customremoved from the cold bath
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customyielding 0.102 g, 76%

Sources & evidence

ORD record
ord-5053432a06e84a109caf025e03967898
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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