Triethylamine → tert-Butyl 3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(4-phenylpiperidine-1-carbonyl)phenyl]piperidine-1-carboxylate

HRID 1176517Notes

Reaction equation

HRID 1176517 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH:30]2[O:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]3[O:52][CH2:51][C:50](=[O:53])[N:49]([CH2:54][CH2:55][CH2:56][O:57][CH3:58])[C:48]=3[CH:59]=2)=[CH:25][CH:24]=1)=[O:22].C(=O)([O-])O.[Na+]>ClCCl>[CH3:58][O:57][CH2:56][CH2:55][CH2:54][N:49]1[C:48]2[CH:59]=[C:44]([CH2:43][O:42][CH:30]3[CH:29]([C:26]4[CH:27]=[CH:28][C:23]([C:21]([N:10]5[CH2:11][CH2:12][CH:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)[CH2:8][CH2:9]5)=[O:22])=[CH:24][CH:25]=4)[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31]3)[CH:45]=[CH:46][C:47]=2[O:52][CH2:51][C:50]1=[O:53]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 698734-PhenylpiperidineHCID 516892Sodium BicarbonateHCID 86610013tert-Butyl 4-(4-chlorocarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Product 1

HCID 68504417tert-Butyl 3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(4-phenylpiperidine-1-carbonyl)phenyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.122 g of 4-phenylpiperidine in 2 ml of dichloromethane is admixed with 0.101 ml of triethylamine. The reaction solution is cooled to 0° and a solution of tert-butyl 4-(4-chlorocarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate in 4 ml of dichloromethane is added dropwise. The reaction mixture is stirred at 0° C. over 40 minutes and subsequently poured onto 25 ml of saturated sodium hydrogencarbonate solution. The mixture is extracted with 80 ml of dichloromethane, the phases are separated and the organic phase is washed with 40 ml each of water and brine, dried over sodium sulphate, filtered and concentrated. The residue is purified by means of flash chromatography (SiO2 60F). The title compound is obtained as a colourless oil. Rf=0.20 (3:1 EtOAc-heptane); Rt=5.44.

Workup

  1. temperatureThe reaction solution is cooled to 0°
  2. extractionThe mixture is extracted with 80 ml of dichloromethane
  3. customthe phases are separated
  4. washthe organic phase is washed with 40 ml each of water and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by means of flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-515278d989914433bc354934a6cc69e0
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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