1,4-Dioxane hydrochloride → 1-[2-(Aminomethyl)-4-chlorophenyl]pyrrolidin-2-one hydrochloride

HRID 1014024Notes

Reaction equation

HRID 1014024 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[O:22])=[C:6]([CH:16]=1)[CH2:7][NH:8]C(=O)OC(C)(C)C.Cl.O1CCOCC1>C(OCC)(=O)C>[ClH:1].[NH2:8][CH2:7][C:6]1[CH:16]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[O:22]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66877767t-Butyl [5-chloro-2-(2-oxopyrrolidin-1-yl)benzyl]carbamate

Product 1

HCID 668776441-[2-(Aminomethyl)-4-chlorophenyl]pyrrolidin-2-one hydrochlorideYield 110.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(Step 3) To a solution (83 ml) of t-butyl [5-chloro-2-(2-oxopyrrolidin-1-yl)benzyl]carbamate obtained in Step 2 (2.70 g) in ethyl acetate was added 4N hydrogen chloride-dioxane solution (7.27 ml) at 0° C., and the mixture was stirred overnight at room temperature. The purified white crystals were collected by filtration, and washed with ethyl acetate to give 1-[2-(aminomethyl)-4-chlorophenyl]pyrrolidin-2-one hydrochloride (1.20 g).

Workup

  1. filtrationThe purified white crystals were collected by filtration
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-c7925f92351d497d9d99cf515835827c
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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