Ethyl Acetate → HCID 19029401, compound

HRID 2256308Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:23][CH2:24]OS(C)(=O)=O)[CH2:10][C:11]([N:13]([CH3:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:30]1([C:36]2([OH:42])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:23][CH2:24][N:39]2[CH2:40][CH2:41][C:36]([OH:42])([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:37][CH2:38]2)[CH2:10][C:11]([N:13]([CH3:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 60 °C

Procedure

3,4-Dichloro-beta-(2-methanesulfonyloxyethyl)-N-methyl-N-(4-methoxyphenyl)benzene propanamide (4.2 g) in DMF (20 mL) was treated with 4-phenyl-4-hydroxypiperidine (1.53 g) and K2CO3 (1.19 g). The mixture was heated at 60° C. for 18 hours. The cooled reaction mixture was diluted the EtOAc (200 mL) and washed with H2O (3×150 mL). The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give an oil. Silica gel chromatography eluting with 90:10 (CH2Cl2 :MeOH) gave the title compound (0.58 g). Mass spectrum (CI): 541.

Workup

customThe cooled reaction mixture
washwashed with H2O (3×150 mL)
dry with materialThe organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give an oil
washSilica gel chromatography eluting with 90:10 (CH2Cl2 :MeOH)

Sources & evidence

ORD record: ord-6cf59d4b5be442f39e0fc91cde3d5272
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654316

Reaction notes

Loading…