Hydrochloric Acid → HCID 11857901, compound

HRID 1710801Notes

Reaction equation

HRID 1710801 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[F:34][C:35]1[CH:40]=[C:39]([C:41]2[O:42][CH:43]=[C:44]([CH2:46][N:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)[N:45]=2)[CH:38]=[CH:37][C:36]=1[OH:53].[N:54]1([CH2:60][CH2:61][CH2:62]O)[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1.Cl>O1CCCC1>[F:34][C:35]1[CH:40]=[C:39]([C:41]2[O:42][CH:43]=[C:44]([CH2:46][N:47]3[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]3)[N:45]=2)[CH:38]=[CH:37][C:36]=1[O:53][CH2:62][CH2:61][CH2:60][N:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 66032Piperidine-1-propanolHCID 5363146Diisopropyl azodicarboxylateHCID 136046542HCID 136046542, compound

Product 1

HCID 11857901HCID 11857901, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (0.81 g, 3.08 mmol, 1 eq) in dry tetrahydrofuran at 0° C. is added dropwise diisopropylazodicarboxylate (0.61 ml, 3.08 mmol, 1 eq). A solution of 2-fluoro-4-[4-(1-piperidinylmethyl)-1,3-oxazol-2-yl]phenol i68 (0.85 g, 3.08 mmol, 1 eq) and 3-(1-piperidinyl)-1-propanol (0.44 g, 3.08 mmol, 1 eq) in tetrahydrofuran is added dropwise to the mixture at 0° C. After 2 days, the mixture is poured onto 0.5 N hydrochloric acid and extracted with diethyl ether. The aqueous phase is basified with 1 N sodium hydroxide to pH 9 and extracted with ethyl acetate. The organic layer is dried on magnesium sulfate and concentrated under reduced pressure. The crude product is purified by chromatography over silica gel to afford 0.25 g of 1-(3-{2-fluoro-4-[4-(piperidin-1-ylmethyl)-1,3-oxazol-2-yl]phenoxy}propyl)piperidine 88 as a yellow oil.

Workup

  1. extractionextracted with diethyl ether
  2. extractionextracted with ethyl acetate
  3. customThe organic layer is dried on magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-4f7a077418184084a3d3f2a0740a43a9
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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