Formaldehyde → HCID 54113017, compound

HRID 1763660Notes

Reaction equation

HRID 1763660 reaction equation
N[C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][CH2:7][N:8]3[CH:19]=[CH:18][CH:17]=[C:9]3[C:10](=[CH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:4]=2[CH:3]=1.[CH2:22]=O.[C:24]([BH3-])#[N:25].[Na+]>C(O)(=O)C>[CH3:22][N:25]([CH3:24])[C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][CH2:7][N:8]3[CH:19]=[CH:18][CH:17]=[C:9]3[C:10](=[CH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 54400122HCID 54400122, compound

Product 1

HCID 54113017HCID 54113017, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 9-amino-11-(3-dimethylaminopropylidene)-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepine (2.0 g., 10 mmoles) and 4 ml. (50 mmoles) of 37% aqueous formaldehyde in 15 ml. of acetonitrite is added 1 g. (16 mmoles) of sodium cyano borohydride. A vigorous and exothermic reaction takes place and a dark residue separates. The mixture is stirred for 15 minutes and then glacial acetic acid is added dropwise until the solution tests neutral on wet pH paper. Stirring is maintained for an additional 2 hours. The volatiles are removed under vacuum, and the residue is dissolved in chloroform. The solution is washed with base and with water, dried over sodium sulfate, and concentrated to leave a residue that is purified by chromatography on silica gel. Elution with chloroformmethanol yields 9-dimethylamino-11-(3-dimethylaminopropylidene)-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepine.

Workup

  1. additionof acetonitrite is added 1 g
  2. customA vigorous and exothermic reaction
  3. stirringStirring
  4. temperatureis maintained for an additional 2 hours
  5. customThe volatiles are removed under vacuum
  6. dissolutionthe residue is dissolved in chloroform
  7. washThe solution is washed with base and with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto leave a residue that
  11. customis purified by chromatography on silica gel
  12. washElution with chloroformmethanol

Sources & evidence

ORD record
ord-a16afe413c7446c28a1a9863533d7455
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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