Ethanol → HCID 14627794, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][N:6]([CH2:15][CH2:16]CC#N)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1.[OH-:23].[Na+].[CH2:25]([OH:27])[CH3:26]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][N:6]([CH2:15][CH2:16][CH2:26][C:25]([OH:23])=[O:27])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1Participants
4
Procedure
A solution of 4-[N,N-bis-(3-chlorobenzyl)amino]butyronitrile (8.59 g; 0.026 mol), NaOH (10 g; 0.25 mol) and ethanol (125 ml) was stirred and heated to reflux for 18 hours. After cooling the solvent was evaporated in vacuo and the solid residue taken up in water (75 ml). After further cooling in ice, conc. HCl was added until the mixture was strongly acid (ca. 25 ml required). The initially precipitated oil hardened to a solid, which was collected by filtration and recrystallised from dimethylformamide-ether and then from 10% v/v water-isopropanol followed by dilution with ether. After drying at 45° C./1 mm the hydrochloride hemihydrate salt of the title compound was obtained (5.60 g). m.p. 170°-173° (dec.; softens above 166°).
Workup
- temperatureheated
- temperatureto reflux for 18 hours
- temperatureAfter cooling the solvent
- customwas evaporated in vacuo
- temperatureAfter further cooling in ice
- additionconc. HCl was added until the mixture
- filtrationwas collected by filtration
- customrecrystallised from dimethylformamide-ether
- dry with materialAfter drying at 45° C./1 mm the hydrochloride hemihydrate salt of the title compound
- customwas obtained (5.60 g)
- customm.p. 170°-173° (dec.; softens above 166°)
Sources & evidence
- ORD record
- ord-db0a1c415467490788d8170d1b2a9cc3
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05527955
Reaction notes
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