N-Methylaniline → HCID 20138025, compound

HRID 1253018Notes

Reaction equation

HRID 1253018 reaction equation
Cl.Cl[CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[CH2:6]1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:18][N:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[CH2:6]1

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 14155951HCID 14155951, compound

Product 1

HCID 20138025HCID 20138025, compound

Procedure

A solution of 8-(2-chloroethyl)-6,7,8,9-tetrahydro-6-methyl-5H-pyrido[3,2-c]azepin-5-one hydrochloride in excess N-methylaniline is heated to about 95° C. for 2 days. Excess N-methylaniline is removed at reduced pressure and the residue is taken up in chloroform. The chloroform layer is washed with dilute aqeuous base, decolorized with activated carbon and dried over sodium sulfate, filtered and concentrated. The residue is dissolved in a suitable solvent and purified by high pressure liquid chromatography using a silica gel column and ethyl acetate. The product is recrystallized from ethyl acetate.

Workup

  1. customExcess N-methylaniline is removed at reduced pressure
  2. washThe chloroform layer is washed
  3. additionwith dilute aqeuous base
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in a suitable solvent
  8. custompurified by high pressure liquid chromatography
  9. customThe product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cdfb17d2a1a2425ba27704bdec5c57b8
Source dataset
uspto-grants-1988_05
Patent number
US04746657

Reaction notes

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