2-(2-Bromoethoxy)tetrahydro-2H-pyran → HCID 12109383, compound

HRID 479462Notes

Reaction equation

HRID 479462 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]([CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:28][CH2:27]2)[C:11]1=[O:39].C(N1CCC(N2C(C3C=CC=CC=3)C3C(=CC=CC=3)NC2=O)CC1)C1C=CC=CC=1.O1CCCCC1OCCBr.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[OH:7][CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]([CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:28][CH2:27]2)[C:11]1=[O:39]

Participants

7

Reactant 5

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 9843766HCID 9843766, compoundHCID 18770900HCID 18770900, compound

Product 1

HCID 12109383HCID 12109383, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In similar way as in Preparation example 3, 1-[2-(tetrahydropyran-2-yl)oxyethyl]-3-(1-benzylpiperidin-4-yl)-4-phenyl-3,4-dihydro-2(1H)-quinazolinone was prepared from 99.4 mg (0.25 mmol) of 3-(1-benzylpiperidin-4-yl)-4-phenyl-3,4-dihydro-2(1H)-quinazolinone and 157 mg (0.75 mmol) of 2-(tetrahydropyran-2-yl)oxyethyl bromide as colorless oil. To a solution of the obtained oil in 4 ml of methanol, 57 mg (0.30 mmol) of p-toluenesulfonic acid monohydrate were added and stirred at room temperature for one hour. The reaction liquid was poured into aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. It was washed with saturated brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate, 1/1 to 1/4) to give 100 mg (0.23 mmol) of the title compound as colorless amorphous.

Workup

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washIt was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate, 1/1 to 1/4)

Sources & evidence

ORD record
ord-82cbd18aea3e4e74978ea92df32fa9e6
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

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