1-Chloroethyl chloroformate → HCID 69311606, compound
Reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[C:24]([F:25])[C:17]=3[NH:16][C:15]2=[O:26])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:27]C(OC(Cl)C)=O>ClCCCl>[ClH:27].[F:25][C:24]1[C:17]2[NH:16][C:15](=[O:26])[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:20][CH2:19][C:18]=2[CH:21]=[CH:22][CH:23]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-(1-Benzylpiperidin-4-yl)-9-fluoro-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one (530 mg, 1.500 mmol) was suspended in 1,2-dichloroethane (10 mL). Mixture was cooled to 0° C. 1-Chloroethyl chloroformate (175 μl, 1.603 mmol) was added to the mixture drop-wise. Reaction was then warmed to reflux and held for 45 minutes. Mixture was concentrated by roto-vap. Residue was dissolved in methanol (10 mL). Reaction was warmed to reflux and held with stirring for 3 hours. Mixture was concentrated by roto-vap. Residue was treated with 20 mL acetone and warmed to reflux for 20 minutes. Resulting solids were filtered off and washed with acetone. Title compound was obtained as tan solid in 67% yield. MS (M+H)+=264.4.
Workup
- customReaction
- temperaturewas then warmed
- temperatureto reflux
- concentrationMixture was concentrated by roto-vap
- dissolutionResidue was dissolved in methanol (10 mL)
- customReaction
- temperaturewas warmed
- temperatureto reflux
- concentrationMixture was concentrated by roto-vap
- additionResidue was treated with 20 mL acetone
- temperaturewarmed
- temperatureto reflux for 20 minutes
- customResulting solids
- filtrationwere filtered off
- washwashed with acetone
Sources & evidence
- ORD record
- ord-87b583b4de1a4673b708df68a6b3bdbb
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470680B2
Reaction notes
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