Ethyl Acetate → Benzyl Chloride

HRID 1445278Notes

Reaction equation

HRID 1445278 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:6].CCO[CH2:10][CH3:11].[CH3:12]COC(C)=O>>[CH2:2]([Cl:6])[C:3]1[CH:11]=[CH:10][CH:12]=[CH:5][CH:4]=1.[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 10953452Ether hydrochloride

Product 2

HCID 7503Benzyl ChlorideHCID 31268Pyrrolidine

Procedure

NR2=Pyrrolidine (11f). The HCl salt of 11f was prepared by suspending the free base in EtOAc and adding 1.1 eq HCl/Et2O and stirring for 1 h. Filtration of the resulting solid led to a hygroscopic solid. Yield=72%; 1H NMR (CDCl3) δ 7.93 (d, 1H), 7.79 (d, 1H), 7.49 (t, 1H), 7.22 (d, 2H), 7.11 (d, 2H), 4.50 (m, 5H), 4.17 (s, 2H), 3.40 (m, 2H), 3.25 (m, 4H), 3.13 (m, 2H), 2.99 (m, 2H), 2.00 (m, 2H), 1.83 (m, 2H); MS (ES+=375.38). Anal Calcd. for C23H27ClN4O1 (4 H2O): C, 57.19; H, 7.30; N, 11.60. Found: C, 56.93; H, 7.46; N, 11.74.

Workup

  1. filtrationFiltration of the resulting solid

Sources & evidence

ORD record
ord-77264732676547bc9af72ee3f1eb981b
Source dataset
uspto-grants-2010_02
Patent number
USRE041150E1

Reaction notes

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