Bis(2-bromoethyl) ether → 4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

HRID 272857Notes

Reaction equation

HRID 272857 reaction equation
[H-].[Na+].[N:3]1([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]#[N:20])=[CH:14][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br>CN(C=O)C>[N:3]1([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3([C:19]#[N:20])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:16][CH:17]=2)[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydride2×HCID 23091635[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]acetonitrile

Product 1

HCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

NaH (14.6 g, 0.61 mol) was suspended in DMF (100 mL). [4-(3-Pyrrolidin-1-ylpropoxy)phenyl]acetonitrile (25.5 g, 0.10 mol) was dissolved in DMF (100 mL) and added dropwise to the ice-cooled suspension of NaH. The reaction mixture was stirred at room temperature for 30 min followed by dropwise addition of 2-bromoethylether (36.2 g, 0.16 mol) in DMF (200 mL) in ice-cold condition. The reaction mixture was poured into ice-cold water. The solid was filtered, washed with water, dried and the resulting solid was washed with 5% EtOAc in hexane to give the title compound (22 g, 67%).

Workup

  1. temperaturecooled
  2. additionThe reaction mixture was poured into ice-cold water
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried
  6. washthe resulting solid was washed with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-0be8e55b96ec4a3aba82a9ad9b4702d9
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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