Formaldehyde → HCID 22368323, compound

HRID 1496854Notes

Reaction equation

HRID 1496854 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH2:13]=O>C(O)=O>[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][N:8]([CH3:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 468400337-Bromo-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 22368323HCID 22368323, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

2.43 g 7-Bromo-2,3,4,5-tetrahydro-1H-benzo[d]azepine are dissolved in 4.055 g of formic acid and 3.2 mL of formaldehyde solution was added. The mixture was stirred at 70° C. for 3.5 h and continued overnight at 25° C. The mixture was concentrated, diluted with water and 10 N NaOH to adjust to a basic pH. The mixture was then extracted with tertbutylmethylether (3×) and the organic phase dried (Na2SO4), filtered and concentrated to yield 2.48 g 7-bromo-3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine as oil.

Workup

  1. waitcontinued overnight at 25° C
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water and 10 N NaOH
  4. extractionThe mixture was then extracted with tertbutylmethylether (3×)
  5. dry with materialthe organic phase dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-02668b2cec53428a962c4ba39e8f78a8
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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