Ethanol → Diethylamine

HRID 406502Notes

Reaction equation

HRID 406502 reaction equation
[CH3:1][C:2]1([N:7]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3]1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:23]([NH:25][CH2:26][C:27](O)=[O:28])=[O:24].CO.C(O)C>CCCCCCC>[Cl:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:23]([NH:25][CH2:26][C:27]([N:4]1[CH2:5][CH2:6][C:2]([CH3:1])([N:7]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH2:3]1)=[O:28])=[O:24].[CH2:3]([NH:4][CH2:5][CH3:6])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 260363N-(3,4-Dichlorobenzoyl)glycineHCID 68902892HCID 68902892, compound

Product 2

HCID 8021DiethylamineYield 0.2%HCID 59764698HCID 59764698, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The title compound was prepared (as a mixture of two enantiomers) from 1-(3-methylpyrrolidin-3-yl)-4-phenylpiperidine and 2-(3,4-dichlorobenzamido)acetic acid using general procedure G. HPLC (Table 1, Method b) Rt 2.13 min; m/z: (M+H)+ 474. From the mixture, the enantiomers were isolated via chiral preparative RP-HPLC (isocratic 10% methanol:10% ethanol:80% heptane:0.2% diethylamine modifier at 15 mL/min, column temperature 50° C.; UV detection monitored at 254 nm; Daicel OD-H column, 20×250 mm, 5 um particle) to yield two isomers, (S)- and (R)-3,4-dichloro-N-(2-(3-methyl-3-(4-phenylpiperidin-1-yl)pyrrolidin-1-yl)-2-oxoethyl)benzamide. The absolute stereochemistry of the isomers was not assigned. Isomer 1 eluted at Rt 11.5-14 min. Isomer 2 eluted at Rt 14.8-18 min.

Sources & evidence

ORD record
ord-3c7b1d2a56c243dca7584c8147f9a064
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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