Piperidine → 7,8-Dimethoxy-1-methyl-5-(piperidin-1-yl)-1,3-dihydro-1,4-benzodiazepin-2-one

HRID 1297098Notes

Reaction equation

HRID 1297098 reaction equation
Cl[C:2]1[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[N:6]([CH3:17])[C:5](=[O:18])[CH2:4][N:3]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CCO>[CH3:16][O:15][C:10]1[C:11]([O:13][CH3:14])=[CH:12][C:7]2[N:6]([CH3:17])[C:5](=[O:18])[CH2:4][N:3]=[C:2]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 691548525-Chloro-7,8-dimethoxy-1-methyl-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 573990387,8-Dimethoxy-1-methyl-5-(piperidin-1-yl)-1,3-dihydro-1,4-benzodiazepin-2-oneYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

Heat at 110° C. in a sealed tube a mixture of 100 mg (0.37 mmol) of 5-chloro-7,8-dimethoxy-1-methyl-1,3-dihydro-1,4-benzodiazepin-2-one XVIIIaa and 300 μl (3 mmol) of piperidine in 10 ml of EtOH for 48 hours. Evaporate to dryness and purify by silica chromatography (CH2Cl2 50/AcOEt 40/EtOH 10). Triturate in hexane, filter, dry. One obtains 70 mg of a beige powder. Yield: 60%. M=125–127° C. 1H-NMR (200 MHz, DMSO): δ 1.63–1.70 (m, 6H, 3×CH2), 3.20–3.23 (m, 4H, 2×CH2), 3.37 (s, 3H, NCH3), 3.91 (AB system, Δδ=0.71, JAB=11.5, 2H, 3-CH2), 3.94 (s, 3H, OCH3), 3.97 (s, 3H, OCH3), 6.73 (s, 1H Ar), 6.99 (s, 1H Ar).

Workup

  1. customEvaporate to dryness
  2. custompurify by silica chromatography (CH2Cl2 50/AcOEt 40/EtOH 10)
  3. customTriturate in hexane
  4. filtrationfilter
  5. customdry

Sources & evidence

ORD record
ord-a87ab1d757794cb7a96604c8b54cc714
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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