Hydrochloric Acid → 1-(4-Nitrophenyl)pyrrolidin-3-ylamine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([NH:15]C(=O)C)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[OH-].[Na+]>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
100 g (0.4 mol) of N-[1-(4-nitrophenyl)-pyrrolidin-3-yl]acetamide (1) are introduced as a suspension into a solution containing 300 ml of 37% hydrochloric acid and 660 ml of water in a 2 l three-necked flask. The reaction medium is heated at 90° C. for 7 hours 45 minutes. After cooling, the medium is neutralized carefully with 300 ml of aqueous 35% sodium hydroxide (pH=approximately 8). The resulting solid is then filtered off, after which it is washed with water (until the washing waters are neutral). The product is then dried under vacuum over P2O5. 74 g (89%) of 1-(4-nitrophenyl)pyrrolidin-3-ylamine (2) are thus obtained in the form of a yellow solid.
Workup
- temperatureAfter cooling
- filtrationThe resulting solid is then filtered off
- washafter which it is washed with water (until the washing waters
- dry with materialThe product is then dried under vacuum over P2O5
Sources & evidence
- ORD record
- ord-b4bac22d49d34936a327e689e7ac90cf
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179301B2
Reaction notes
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