Ethyl Acetate → HCID 19029358, compound

HRID 2256303Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:22][CH2:23]OS(C)(=O)=O)[CH2:10][C:11]([N:13]([CH3:21])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:29]1([C:35]2(O)[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:42]([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]([CH3:21])[C:11](=[O:12])[CH2:10][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:22][CH2:23][N:38]2[CH2:37][CH2:36][CH:35]([CH2:29][C:34]3[CH:42]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:40][CH2:39]2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3,4-Dichloro-beta-(2-methanesulfonyloxyethyl)-N-methyl-N-(4-chlorophenyl)benzene propanamide (1.6 g) in DMF (10 mL) was treated with 4-phenyl-4-hydroxypiperidine (1.14 g) and K2CO3 (0.476 g). The mixture was heated at 60° C. for 18 hours. The cooled reaction mixture was diluted the EtOAc (100 mL) and washed with H2O (2×100 mL). The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give an oil. Silica gel chromatography eluting with 95:5 (CH2Cl2 :MeOH) gave the title compound (0.56 g). M.p. 67°-72°, Mass spectrum (CI): 543.

Workup

customThe cooled reaction mixture
washwashed with H2O (2×100 mL)
dry with materialThe organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give an oil
washSilica gel chromatography eluting with 95:5 (CH2Cl2 :MeOH)

Sources & evidence

ORD record: ord-52af8958d2e743098dca6a8c629148b4
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654316

Reaction notes

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