Pyrrolidine → 5-Nitro-2-(2-pyrrolidin-1-ylethyl)benzoxazole

HRID 735098Notes

Reaction equation

HRID 735098 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH:12]=[CH2:13])=[N:9][C:8]=2[CH:14]=1)([O-:3])=[O:2].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH2:12][CH2:13][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[N:9][C:8]=2[CH:14]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 688156545-Nitro-2-vinylbenzoxazole

Product 1

HCID 688160345-Nitro-2-(2-pyrrolidin-1-ylethyl)benzoxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1 g (5.25 mmol) of 5-nitro-2-vinylbenzoxazole and 0.66 mL (8 mmol) of pyrrolidine in 8 mL of ethanol is stirred for 2 hours at ambient temperature. Then the reaction solution is evaporated down. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia (20:1:0.1)). Yield: 0.74 g (53.9% of theory); C13H15N3O3 (M=261.28); calc.: molecular ion peak (M+H)+: 262; found: molecular ion peak (M+H)+: 262; Rf value: 0.2 (silica gel, dichloromethane/ethanol/ammonia (20:1:0.1)).

Workup

  1. customThen the reaction solution is evaporated down
  2. customThe purification

Sources & evidence

ORD record
ord-db092501c5b6433e8db2b0272e5a8600
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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