11-Chloro-6,11-dihydrodibenz[b,e]oxepin → N-{4-[1-(6,11-Dihydrodibenzo[b,e]-oxepin-11-yl)-piperidine-4-yl]-butyl}-3-(pyridin-3-yl)-propionamide

HRID 1178400Notes

Reaction equation

HRID 1178400 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.Cl.Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:39])[CH2:31][CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)[CH2:21][CH2:20]1>ClCCl>[CH:16]1[C:3]2[CH:2]([N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:39])[CH2:31][CH2:32][C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)[CH2:21][CH2:20]3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[CH2:6][O:5][C:4]=2[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 1296214811-Chloro-6,11-dihydrodibenz[b,e]oxepinHCID 18425746N-(4-piperidin-4-yl-butyl)-3-pyridin-3-yl-propionamide dihydrochloride

Product 1

HCID 15390851N-{4-[1-(6,11-Dihydrodibenzo[b,e]-oxepin-11-yl)-piperidine-4-yl]-butyl}-3-(pyridin-3-yl)-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.46 g (15 mmol) 11-chloro-6,11-dihydrodibenzo[b,e]oxepine are dissolved in 90 ml absolute dichloromethane and 5.43 g (15 mmol) N-(4-piperidin-4-yl-butyl)-3-pyridin-3-yl-propionamide dihydrochloride is added. 5.0 g (49.5 mmol) TEA is dissolved in 20 ml absolute dichloromethane and added dropwise under ice cooling. The mixture is stirred for two days at RT without further cooling. Subsequently, the batch is washed twice, each with 50 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The resinous residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5) and after drawing off the solvent, is first crystallized twice, each from 10 ml 1-chlorobutane and subsequently once from 10 ml acetic acid ethyl ester. Colorless crystals with a MP of 110-112° C. in a yield of 0.2 g (3%) are recovered

Workup

  1. additionadded dropwise under ice cooling
  2. washSubsequently, the batch is washed twice
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is removed under vacuum
  5. customThe resinous residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5)
  6. customis first crystallized twice
  7. customColorless crystals with a MP of 110-112° C. in a yield of 0.2 g (3%) are recovered

Sources & evidence

ORD record
ord-c6c67c7b1d9b4ab8aa031f0d41ffc35e
Source dataset
uspto-grants-2007_10
Patent number
US07276524B2

Reaction notes

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