Chloroacetone → HCID 66970969, compound

HRID 1361527Notes

Reaction equation

HRID 1361527 reaction equation
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:28][C:29](=[O:31])[CH3:30].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>CN(C=O)C>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:28][C:29](=[O:31])[CH3:30])[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 66971095HCID 66971095, compound

Product 1

HCID 66970969HCID 66970969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1-((1S,2R,4R)-Bicyclo[2.2.1]heptan-2-yl)piperidin-4-yl)phenol (compound no. 229) (27.0 mg, 0.1 mmol) was dissolved in DMF (0.5 mL) and treated with K2CO3 (100 mg, 0.72 mmol) followed by the 1-chloropropan-2-one (19 mg, 0.4 mmol) and Nal (100 mg, 0.66 mmol) and the reaction was allowed to stir at room temperature for 48 h. The crude reaction mixture was filtered, diluted with DMSO to 1 mL and purified by LC/MS (10-99 CH3CN—H2O gradient with 0.03% TFA, 9 minute) to provide 1-(2-(1-((1S,2R,4R)-bicyclo[2.2.1]heptan-2-yl)piperidin-4-yl)phenoxy)propan-2-one (compound no. 53) as the TFA salt. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 327.0 [M+H]+, retention time 2.32 min.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. additiondiluted with DMSO to 1 mL
  4. custompurified by LC/MS (10-99 CH3CN—H2O gradient with 0.03% TFA, 9 minute)

Sources & evidence

ORD record
ord-61b7246de4f9473ebb517f7606b3dfb5
Source dataset
uspto-grants-2011_02
Patent number
US07880007B2

Reaction notes

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