1,1-Dimethoxyethyl(dimethyl)amine → HCID 69844443, compound
Reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.CO[C:28](OC)([N:30]([CH3:32])[CH3:31])[CH3:29]>>[CH3:31][N:30]([CH3:32])[C:28]([CH3:29])=[CH:24][C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:15]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:16])=[CH:22][CH:21]=1)=[O:25]Participants
3
Procedure
A mixture of 1-[4-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-phenyl]-ethanone (2.0 g) and dimethylacetamide dimethylacetal (15 ml) was refluxed in an inert atmosphere for 15 hours and the volatiles were removed at reduced pressure. The crude solid was dissolved in dichloromethane and filtered through a short column of hydrous sodium magnesium silicate followed by several volumes of dichloromethane. The combined eluant was concentrated and hexane was gradually added until crystallization occurred. The cooled solution was filtered to recover the title compound (1.03 g) as a crystalline solid, m.p. 183-185° C.
Workup
- temperaturewas refluxed in an inert atmosphere for 15 hours
- customthe volatiles were removed at reduced pressure
- dissolutionThe crude solid was dissolved in dichloromethane
- filtrationfiltered through a short column of hydrous sodium magnesium silicate
- concentrationThe combined eluant was concentrated
- additionhexane was gradually added until crystallization
- filtrationThe cooled solution was filtered
- customto recover the title compound (1.03 g) as a crystalline solid, m.p. 183-185° C.
Sources & evidence
- ORD record
- ord-18bf75318db24093b016ed146f6a1154
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06831079B1
Reaction notes
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