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 1280765Notes

Reaction equation

HRID 1280765 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 abs dichloromethane and 5.43 g (15 mmol) N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide dihydrochloride are added. 5.0 g (49.5 mmol) TEA are dissolved in 20 ml abs. dichloromethane and added dropwise under ice cooling. The mixture is stirred without further cooling for two days at RT. Subsequently, the batch is washed twice each with 50 ml water. The organic phase is dried over silica gel with CHCl3/CH2OH (95/5) and crystallized twice at first, each from 10 ml 1-chlorobutane, and subsequently crystallized once from 10 ml acetic acid. Colorless crystals with a MP of 110-112° C. were isolated; yield: 0.2 g (3%).

Workup

  1. additionare added
  2. washSubsequently, the batch is washed twice each with 50 ml water
  3. dry with materialThe organic phase is dried over silica gel with CHCl3/CH2OH (95/5)
  4. customcrystallized twice at first, each from 10 ml 1-chlorobutane
  5. customsubsequently crystallized once from 10 ml acetic acid
  6. customColorless crystals with a MP of 110-112° C. were isolated

Sources & evidence

ORD record
ord-b8632126d3324242b339c773d0138f3e
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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