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Sodium hydride → Benzyl 3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(3-phenylpyrrolidin-1-ylmethyl)phenyl]piperidine-1-carboxylate

HRID 1176588
Notes
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Reaction equation

HRID 1176588 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH:10]2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]3[O:35][CH2:34][CH2:33][N:32]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:31]=3[CH:41]=2)=[CH:5][CH:4]=1.[C:42]1([CH:48]2[CH2:52][CH2:51][NH:50][CH2:49]2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[H-].[Na+]>CN(C)C=O.COC(C)(C)C>[CH3:40][O:39][CH2:38][CH2:37][CH2:36][N:32]1[C:31]2[CH:41]=[C:27]([CH2:26][O:25][CH:10]3[CH:9]([C:6]4[CH:7]=[CH:8][C:3]([CH2:2][N:50]5[CH2:51][CH2:52][CH:48]([C:42]6[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=6)[CH2:49]5)=[CH:4][CH:5]=4)[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[O:16])[CH2:11]3)[CH:28]=[CH:29][C:30]=2[O:35][CH2:34][CH2:33]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 31467433-PhenylpyrrolidineHCID 68501265HCID 68501265, compound

Product 1

HCID 68503996Benzyl 3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(3-phenylpyrrolidin-1-ylmethyl)phenyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

The stirred solution of 0.0435 g of benzyl 4-(4-chloromethylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate (Example 270b) and 0.0155 g of 3-phenylpyrrolidine in 0.5 ml of N,N-dimethylformamide is admixed at 0° C. with 0.0076 g of sodium hydride dispersion (60% in oil). The reaction mixture is stirred at 0° C. over 15 minutes, then at room temperature for 1 hour, and subsequently diluted with 80 ml of tert-butyl methyl ether. The mixture is washed with 20 ml of water, then 10 ml of brine, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rt=4.72.

Workup

  1. waitat room temperature for 1 hour
  2. washThe mixture is washed with 20 ml of water
  3. dry with material10 ml of brine, dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-dfd5ca1c79744933925e94b581bf2ebc
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842688B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes