Cyclohexylamine → HCID 70606654, compound

HRID 1863098Notes

Reaction equation

HRID 1863098 reaction equation
CS(OCCCOC(C1N=C(C2C=CC=CC=2)C2C=C([Cl:29])C=CC=2N(C)C1=O)=O)(=O)=O.C1(N)CCCCC1.[CH:39]1([NH:45][CH2:46][CH2:47][CH2:48][O:49][C:50]([CH:52]2[N:58]=[C:57]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:56]3[CH:65]=[C:66]([Cl:69])[CH:67]=[CH:68][C:55]=3N(C)C2=O)=[O:51])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>CC(C)=O>[ClH:29].[CH:39]1([NH:45][CH2:46][CH2:47][CH2:48][O:49][C:50]([C:52]2[NH:58][C:57]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[C:56]3[C:55]=2[CH:68]=[CH:67][C:66]([Cl:69])=[CH:65]3)=[O:51])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 54455760HCID 54455760, compoundHCID 54456826HCID 54456826, compound

Product 1

HCID 70606654HCID 70606654, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid 3-[(methylsulfonyl)oxy]propyl ester in 400 ml. of acetone is treated with 100 ml. of cyclohexylamine and the mixture is boiled at reflux for 2 hours. The mixture is then concentrated to dryness under reduced pressure and the residue dissolved in 300 ml. of benzene. After washing with water, the organic solution is shaken with an excess of 2-N hydrochloric acid. The clear aqueous phase is made alkaline with 2-N sodium carbonate solution and the liberated base extracted with benzene. The benzene extract is washed with water, dried over sodium sulfate and concentrated to dryness. The oily residue crystallizes upon trituration with diethyl ether, and there are obtained 22.4 g. of 7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid 3-(cyclohexylamino)propyl ester having a melting point of 109°-111° C.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe mixture is then concentrated to dryness under reduced pressure
  3. dissolutionthe residue dissolved in 300 ml
  4. washAfter washing with water
  5. extractionthe liberated base extracted with benzene
  6. extractionThe benzene extract
  7. washis washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to dryness
  10. customThe oily residue crystallizes upon trituration with diethyl ether, and there
  11. customare obtained 22.4 g

Sources & evidence

ORD record
ord-44cac721fe0242389717a15c423cd01c
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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