Ammonia → 1,1a,6,10b-Tetrahydrodibenzo[b,f]cyclopropa[d]azepine

HRID 1730262Notes

Reaction equation

HRID 1730262 reaction equation
N.Cl[C:3]1(Cl)[CH:10]2[CH:4]1[C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[N:7](C=O)[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=12.[Na].[Cl-].N>>[CH2:3]1[CH:4]2[CH:10]1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=12

Participants

5

Reactant 4

HCID 222AmmoniaHCID 5360545SodiumHCID 12412205HCID 12412205, compoundHCID 20976574Ammonia chloride

Product 1

HCID 3252711,1a,6,10b-Tetrahydrodibenzo[b,f]cyclopropa[d]azepineYield 53%

Procedure

In 20 ml. of liquid ammonia is suspended 1.824 g. of 1,1-dichloro-1a,10b-dihydrodibenzo(b,f)cycloprop(d)azepine-6(1H)-carboxaldehyde, and while the suspension is stirred at -40° to -50° C,0.69 g. of small pieces of sodium metal are added. The system is stirred atthe same temperature for 1 hour, after which time 1.5 g. of ammonia chloride is added. The liquid ammonia is distilled off and 20 ml. of wateris added. The mixture is extracted three times with 20 ml. portions of benzene and the extracts are washed with water and dried. The benzene extracts are passed over a column packed with silica gel and then adsorbedmaterial is eluted by means of a mixed solvent of benzenecyclohexane (6:4).The eluate is concentrated, whereby 0.658 g. (53 %) of 1,1a,6,10b-tetrahydrodibenzo(b,f)cycloprop(d)azepine is obtained.

Workup

  1. distillationThe liquid ammonia is distilled off
  2. additionof wateris added
  3. extractionThe mixture is extracted three times with 20 ml
  4. washportions of benzene and the extracts are washed with water
  5. customdried
  6. washadsorbedmaterial is eluted by means of a mixed solvent of benzenecyclohexane (6
  7. concentration4).The eluate is concentrated

Sources & evidence

ORD record
ord-00ea9da9b524444ebc40c9d5ce7b20ce
Source dataset
uspto-grants-1976_11
Patent number
US03992370

Reaction notes

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