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Potassium Carbonate → HCID 89437167, compound

HRID 1410553
Notes
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Reaction equation

HRID 1410553 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][N:5]1[CH2:12][CH2:11][C:8]2([O:10][CH2:9]2)[CH2:7][CH2:6]1.[OH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl.CCO>C(O)C.C(OCC)(=O)C.CN(C)C=O>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][N:5]1[CH2:12][CH2:11][C:8]([CH2:9][N:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]2=[O:17])([OH:10])[CH2:7][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 21887872Ethanol hydrochlorideHCID 86695293HCID 86695293, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 89437167HCID 89437167, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 21584252Ethanol ethylacetateSolvent

Procedure

23.00 g (0.104 mol) of N-(2-fluorobenzyl)-1-oxa-6-azaspiro[2,5]-octane and 10.30 g (0.108 mol) of 2-hydroxy-pyridine were weighed and added into 80 mL N,N-dimethylformamide, and then 1.00 g (0.007 mol) potassium carbonate was added. The reaction was stirred and reacted at a bath temperature of about 80° C. for 1 day, and the solvent was recovered. Potassium carbonate aqueous solution was added into the residue The mixture was extracted with dichloromethane twice, combined, washed with water, and dried. The solvent was recovered, crystallized with petroleum ether-ethyl acetate to obtain colorless flake-like crystal, 22.80 g, yield 69.3%. 1H-NMR (CDCl3, ppm) δ: 7.372 (2H, m), 7.228 (2H, m), 7.092 (1H, t, J=7.56 Hz), 7.020 (1H, t, J=8.96 9.24 Hz), 6.639 (1H, d, J=9.24 Hz), 6.228 (1H, t×d, J1=6.72 Hz, J2=1.12 Hz), 4.720 (1H, s), 4.036 (2H, s), 3.603 (2H, s), 2.69 (2H, dd, J1=7.84 Hz, J2=3.64 Hz), 2.46 (2H, t×d, J1=8.40 Hz, J2=2.80 Hz), 1.55-1.74 (4H, m). The product was heated and dissolved in ethanol-ethyl acetate, salified with HCl-EtOH while warm and naturally cooled to obtain a colorless fine granular crystal, which was dried under vacuum to obtain 20.00 g product. Melting point: 249-251° C.

Workup

  1. customreacted at a bath temperature of about 80° C. for 1 day
  2. customthe solvent was recovered
  3. additionPotassium carbonate aqueous solution was added into the residue The mixture
  4. extractionwas extracted with dichloromethane twice
  5. washwashed with water
  6. customdried
  7. customThe solvent was recovered
  8. customcrystallized with petroleum ether-ethyl acetate
  9. customto obtain colorless flake-like crystal, 22.80 g, yield 69.3%
  10. temperatureThe product was heated
  11. temperaturewhile warm
  12. temperaturenaturally cooled
  13. customto obtain a colorless fine granular crystal, which
  14. customwas dried under vacuum

Sources & evidence

ORD record
ord-673e07b9c349442b936b17a0c92474ea
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921563B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes