Hydrochloric Acid → HCID 67263856, compound

HRID 1041587Notes

Reaction equation

HRID 1041587 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:8][CH2:7][CH2:6][N:5]([C:9](=O)[CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:4]2[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:3]1=2.Cl>O1CCCC1>[CH3:1][C:2]1([CH3:24])[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[C:4]2[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:3]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67264680HCID 67264680, compound

Product 1

HCID 67263856HCID 67263856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

1-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-2-pyrrolidin-1-yl-ethanone (0.508 g, 0.00153 mol), 1.00 M of Borane-THF complex in tetrahydrofuran (7.7 mL; Acros) and anhydrous tetrahydrofuran (12.4 mL) were combined in a round bottom flask and heated to 70° C. for 6.5 hours. Concentrated HCl was added dropwise until gas evolution stopped. Solvent was removed under reduced pressure, then an additional 5 mL of conc. HCl was added until the mixture was pH 1. The reaction was heated at 100° C. for 1.5 hours. The reaction was removed from the heat and 10 N NaOH (6 mL) was added until the mixture was pH 7-8. Na2CO3 was added until the solution was pH 11. The solution was extracted twice into DCM, and the combined organic layers were dried with sodium sulfate, filtered and concentrated under reduced pressure to yield a crude brown oil, 5,5-Dimethyl-8-nitro-1-(2-pyrrolidin-1-yl-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine. LCMS: m/z=332.35 (M+H+).

Workup

  1. customSolvent was removed under reduced pressure
  2. additionan additional 5 mL of conc. HCl was added until the mixture
  3. temperatureThe reaction was heated at 100° C. for 1.5 hours
  4. customThe reaction was removed from the
  5. temperatureheat
  6. addition10 N NaOH (6 mL) was added until the mixture
  7. additionNa2CO3 was added until the solution
  8. extractionThe solution was extracted twice into DCM
  9. dry with materialthe combined organic layers were dried with sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-820b51cc086e4b60a6110f4819724e14
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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