Formaldehyde → HCID 10149289, compound

HRID 505018Notes

Reaction equation

HRID 505018 reaction equation
B(F)(F)F.CCO[CH2:8][CH3:9].[NH:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=CC=N1.[CH:21]1[CH2:25][CH2:24][CH2:23]C=1.C=O.[C:28](#[N:30])[CH3:29]>>[CH:18]1[CH:19]=[CH:20][C:15]2[CH2:14][NH:30][CH2:28][CH2:29][N:10]3[C:16]=2[C:17]=1[CH:9]1[CH2:8][CH2:23][CH2:24][CH:25]1[CH2:21]3

Participants

6

Reactant 5

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 8000Boron trifluoride etherateHCID 8882CyclopenteneHCID 134664Benzodiazepine

Product 1

HCID 10149289HCID 10149289, compoundYield 53%

Conditions

Temperature
45 °C

Procedure

BF3.OEt2 (2.2 ml, 17.5 mmol) was dropped to a mixture of benzodiazepine (0.74 g, 5 mmol), cyclopentene (3.6 ml, 40.0 mmol), paraformaldehyde (165 mg, 5.5 mmol) in acetonitrile (20 ml) at room temperature. The mixture was heated at 45° C. (oil bath) for 5 h. It was concentrated in vacuo. The residue was taken up with EtOAc (150 ml) and washed first with a mixture of aqueous Na2CO3 and NaOH (200 ml), and then with brine (200 ml). The organic layer was dried and added HCl (1 N in diethyl ether, 10 ml) and the resultant precipitates were collected by filtration. The mixture was purified by flash chromatography on silica gel (5-15% MeOH in CH2Cl2) to afford E (0.70 g, 53% yield.)

Workup

  1. concentrationIt was concentrated in vacuo
  2. washwashed first with a mixture of aqueous Na2CO3 and NaOH (200 ml)
  3. customThe organic layer was dried
  4. additionadded HCl (1 N in diethyl ether, 10 ml)
  5. customthe resultant precipitates
  6. filtrationwere collected by filtration
  7. customThe mixture was purified by flash chromatography on silica gel (5-15% MeOH in CH2Cl2)
  8. customto afford E (0.70 g, 53% yield.)

Sources & evidence

ORD record
ord-42e8527601ef4e85ba39dab6c9382524
Source dataset
uspto-grants-2010_08
Patent number
US07781427B2

Reaction notes

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