Hydrochloric Acid → HCID 58258491, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][C:3]=1[CH2:14][C:15](N1CCCC1)=[O:16].Cl.[O:23]1CCOCC1>>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1[CH2:14][C:15]([OH:16])=[O:23]Participants
Procedure
A solution of 1-[[2-chloro-4-(1-pyrrolidinylmethyl)phenyl]acetyl]-pyrrolidine (crude, max. 44.70 mmol) in dioxane (100 ml) was stirred at r.t. A 6 M HCl solution was added. The mixture was stirred and refluxed for 3 days. The mixture was concentrated in vacuo. The residue was taken up in water and the mixture was brought to pH 10 with a 4 N NaOH solution. The solution was washed with diethyl ether (3×40 ml). The aqueous layer was acidified to pH 3 with a 6 N HCl solution. The mixture was concentrated in vacuo. The residue was purified by neutral high performance liquid chromatography (Column: Lana 300×50 mm, 10 μm; Mobile Phase: 0-20% CH3CN in water; Flow Rate: 80 ml/min; Finished Time: 25 min). The desired fraction was collected and evaporated in vacuo. Yield: 2.8 g of 2-chloro-4-(1-pyrrolidinylmethyl)-benzeneacetic acid (25% yield over last 3 steps).
Workup
- temperaturerefluxed for 3 days
- concentrationThe mixture was concentrated in vacuo
- washThe solution was washed with diethyl ether (3×40 ml)
- concentrationThe mixture was concentrated in vacuo
- customThe residue was purified by neutral high performance liquid chromatography (Column: Lana 300×50 mm, 10 μm; Mobile Phase: 0-20% CH3CN in water; Flow Rate: 80 ml/min; Finished Time: 25 min)
- customThe desired fraction was collected
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-56b7512c226c4c0c80c553c90ad9fb77
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09107946B2
Reaction notes
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