Potassium Carbonate → Oxalate

HRID 572869Notes

Reaction equation

HRID 572869 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.CC(N)([CH2:29][OH:30])C.[C:32](=[O:35])([O-:34])[O-].[K+].[K+].Cl.[NH:39]1[CH2:42][CH:41]([OH:43])[CH2:40]1>[Cu]I>[S:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[CH:8]([O:18][CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[C:4]1[CH:3]=[C:2]([N:39]2[CH2:42][CH:41]([OH:43])[CH2:40]2)[CH:7]=[CH:6][CH:5]=1.[C:29]([O-:30])(=[O:18])[C:32]([O-:34])=[O:35]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 118072-Amino-2-methyl-1-propanolHCID 27592903-Hydroxyazetidine hydrochlorideHCID 569474582-[(3-Iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole

Product 2

HCID 71081OxalateHCID 668358851-{3-[Benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}azetidin-3-ol

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
60 °C

Procedure

A screw-capped tube is charged with 2-[(3-iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (example 41, 150 mg), copper(I) iodide (15 mg), deanol (1 mL), potassium carbonate (306 mg), azetidin-3-ol, hydrochloride (88 mg). The tube is evacuated, filled with argon and sealed. After stirring at 60° C. for 100 h, the mixture is diluted with dichloromethane, water and ammonia. After decantation, the aqueous phase is extracted with dichloromethane. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 95/5/0.5 to 90/10/0.5). The base is converted into its oxalate salt in acetone to give 1-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}azetidin-3-ol, oxalate melting at 117° C.

Workup

  1. customThe tube is evacuated
  2. additionfilled with argon
  3. customsealed
  4. additionthe mixture is diluted with dichloromethane, water and ammonia
  5. extractionAfter decantation, the aqueous phase is extracted with dichloromethane
  6. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 95/5/0.5 to 90/10/0.5)

Sources & evidence

ORD record
ord-6e6c0498cda54f36bcbc663690a7ac65
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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