[1-(2-Chloro-4-nitrophenyl)pyrrolidin-3-yl]dimethylamine → [1-(4-Amino-2-chlorophenyl)pyrrolidin-3-yl]dimethylamine

HRID 69406

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][CH:13]([N:16]([CH3:18])[CH3:17])[CH2:12]1>C(O)(=O)C.[Zn]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:15][CH2:14][CH:13]([N:16]([CH3:17])[CH3:18])[CH2:12]2)=[C:2]([Cl:1])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Zinc powder (3.0 g) was added in portions to a solution of [1-(2-chloro-4-nitrophenyl)-pyrrolidin-3-yl]dimethylamine (1.9 g) in glacial acetic acid (50 mL) cooled to 0° C. After the addition was complete, the mixture was stirred at room temperature for 30 minutes and then insolubles were filtered off with suction. The filtrate was concentrated in a rotary evaporator, and the residue was partitioned between sodium hydroxide solution and ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The product with the molecular weight of 239.75 (C12H18ClN3) was obtained in this way; MS (ESI): 240 (M+H+).

Workup

additionAfter the addition
filtrationinsolubles were filtered off with suction
concentrationThe filtrate was concentrated in a rotary evaporator
customthe residue was partitioned between sodium hydroxide solution and ethyl acetate
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated
customThe product with the molecular weight of 239.75 (C12H18ClN3) was obtained in this way

Sources & evidence

ORD record: ord-98142ce713b848e38dead296824b696e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822495B2

Linked notes

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