Phosphorus oxide (P4O10) → HCID 21414424, compound

HRID 442382Notes

Reaction equation

HRID 442382 reaction equation
[CH3:1][N:2]1[CH2:24][CH2:23][CH:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]([CH3:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)[CH2:4][CH2:3]1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O.[OH-].[NH4+]>CCOCC>[CH3:22][N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:6]([CH:5]2[CH2:23][CH2:24][N:2]([CH3:1])[CH2:3][CH2:4]2)=[N:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

Participants

6

Reactant 4

HCID 14812Phosphorus oxide (P4O10)HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 21414373HCID 21414373, compound

Product 1

HCID 21414424HCID 21414424, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 9 g of crude 1-methyl-2'-(N-methylanilino)isonipecotanilide base, 10 g of phosphorus pentoxide and 30 ml of phosphorus oxychloride is heated under reflux for 4 hours, and the reaction mixture is diluted with ether and slowly added to an ice-cold solution of ammonium hydroxide. The mixture is filtered, and the ether layer is separated, dried over anhydrous potassium carbonate and evaporated to yellow solid residue (8.0 g). This crude cyclized base is dissolved in 100 ml of dilute acetic acid, the solution is clarified with activated charcoal and the filtrate is made basic with ammonium hydroxide. The precipitated base is collected, dissolved in 30 ml of ether, and the ether layer is dried over anhydrous potassium carbonate. This solution is filtered into 100 ml of petroleum ether. The product crystallizes as a yellow solid and is collected and dried in vacuo; 5-methyl-11-(1-methyl-4-piperidyl)-5H-dibenzo[b,e][1,4]-diazepine, m.p. 119°-121° C., is thereby obtained; IR (KBr) 6.15μ (anil C=N).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe mixture is filtered
  4. customthe ether layer is separated
  5. dry with materialdried over anhydrous potassium carbonate
  6. customevaporated to yellow solid residue (8.0 g)
  7. dissolutionThis crude cyclized base is dissolved in 100 ml of dilute acetic acid
  8. customThe precipitated base is collected
  9. dissolutiondissolved in 30 ml of ether
  10. dry with materialthe ether layer is dried over anhydrous potassium carbonate
  11. filtrationThis solution is filtered into 100 ml of petroleum ether
  12. customThe product crystallizes as a yellow solid
  13. customis collected
  14. customdried in vacuo

Sources & evidence

ORD record
ord-9d31d00a9afa4fafb3c3d0a31902a84e
Source dataset
uspto-grants-1977_08
Patent number
US04045445

Reaction notes

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