Dichloromethane → 4-(4-Chlorophenyl)-3-(1-pyrrolidinyl)-butan-2-one

HRID 30372Notes

Reaction equation

HRID 30372 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.[CH2:20](Cl)Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[C:10](=[O:12])[CH3:20])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 22270338HCID 22270338, compound

Product 1

HCID 222704894-(4-Chlorophenyl)-3-(1-pyrrolidinyl)-butan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared according to the procedure of Reference Example 2, Step C except that ethyl 3-(4-chlorophenyl)-2-(1-pyrrolidinyl)-propanoate (from Step A) was the ester used (two steps). TLC Rf=0.7 (95:5 CH2Cl2:MeOH). LC/MS m/e=252 (M+1). 500 MHz 1H NMR (CDCl3) δ 1.86(br s, 4H), 2.03 (s, 3H), 2.66 (m, 2H), 2.78 (m, 2H), 2.98 (dd, J=2.9, 10.3 Hz, 1H), 3.08 (m, 1H), 3.43 (m, 1H), 7.12 (d, J=8.3 Hz, 2H), 7.26 (d, J=8.3 Hz, 2H)

Sources & evidence

ORD record
ord-91384748a3e344d2af4974dd1ebc865a
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Reaction notes

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