Hydrochloric Acid → HCID 21442787, compound

HRID 328590Notes

Reaction equation

HRID 328590 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[N:8]([CH2:17][CH:18]3[O:23][CH2:22][CH2:21][NH:20][CH2:19]3)[C:7]=2[CH:24]=1)[CH3:2].[CH2:25]=O.Cl>C(O)=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[N:8]([CH2:17][CH:18]3[O:23][CH2:22][CH2:21][N:20]([CH3:25])[CH2:19]3)[C:7]=2[CH:24]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 21442794HCID 21442794, compound

Product 1

HCID 21442787HCID 21442787, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 3-ethyl-5-(2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine (0.3 g), 90% formic acid (0.7 g) and 37% formalin (0.58 ml) was stirred at 90°-100° C for 8 hours. After cooling, 4N hydrochloric acid was added to the reaction mixture. The resulting mixture was evaporated to dryness under reduced pressure. Water was added to the residue, neutralized with aqueous ammonia, and extracted with benzene. The benzene extract was washed with water, dried over anhydrous sodium sulfate and evaporated to afford 3-ethyl-5-(4-methyl-2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oily substance. M.P. 168°-170° C (oxalate).

Workup

  1. temperatureAfter cooling
  2. customThe resulting mixture was evaporated to dryness under reduced pressure
  3. additionWater was added to the residue
  4. extractionextracted with benzene
  5. extractionThe benzene extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-4c6ff6d4497344fdb5af47135326b105
Source dataset
uspto-grants-1977_04
Patent number
US04017621

Reaction notes

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