Piperidine → HCID 22312253, compound

HRID 1939161Notes

Reaction equation

HRID 1939161 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl[C:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH3:20])[C:12](=[O:21])[CH2:11][N:10]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:20][N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:9]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:10][CH2:11][C:12]1=[O:21]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 21467080HCID 21467080, compound

Product 1

HCID 22312253HCID 22312253, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperidine (1.34 g) was added to a solution of crude 5-chloro-1,2-dihydro-1-methyl-3H-1,4-benzodiazepin-2-one hydrochloride (0.005 mol) in dichloromethane (50 ml) cooled in ice. After warming to room temperature, sodium bicarbonate solution (20 ml) was added. The organic phase was separated, dried (Na2SO4) and evaporated to give an orange oil which was purified by column chromatography on silica with CH2Cl2 →CH2Cl2 :MeOH 95:5 as eluant to afford 0.62 g of product as an orange gum 1H NMR (250 MHz, CDCl3) δ: 1.5-1.8 (6H, m), 3.15-3.4 (4H, m), 3.4 (3H, s), 3.5 and 4.25 (2H, ABq, J=11Hz), 7.15-7.6 (5H, m).

Workup

  1. temperaturecooled in ice
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give an orange oil which
  6. customwas purified by column chromatography on silica with CH2Cl2 →CH2Cl2 :MeOH 95:5 as eluant

Sources & evidence

ORD record
ord-2930de38db6d415da6bf0dd224b70c87
Source dataset
uspto-grants-1997_12
Patent number
US05696110

Reaction notes

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