6-Benzyl-1-oxa-6-azaspiro(2,5)octane → HCID 54673547, compound

HRID 1410554Notes

Reaction equation

HRID 1410554 reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][C:11]2([O:13][CH2:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16][C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[N:21][CH:22]=1>C(O)C.C(OCC)(=O)C.Cl.CCO>[Br:16][C:17]1[CH:18]=[CH:19][C:20](=[O:23])[N:21]([CH2:12][C:11]2([OH:13])[CH2:14][CH2:15][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10]2)[CH:22]=1

Participants

5

Reactant 2

HCID 892386-Benzyl-1-oxa-6-azaspiro(2,5)octaneHCID 178515818HCID 178515818, compound

Product 1

HCID 54673547HCID 54673547, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 21584252Ethanol ethylacetateSolventHCID 21887872Ethanol hydrochlorideSolvent

Procedure

Referring to the method 2 of Example 1, N-benzyl-1-oxa-6-azaspiro[2,5]-octane and 5-bromo-2-hydroxy-pyridine were used for preparing a free base. Melting point: 146-148° C. The product was dissolved in ethanol-ethyl acetate and salified with HCl-EtOH to obtain a hydrochloride, yield 78.5%. Melting point: 148-150° C. 1H-NMR (D2O, ppm) δ: 7.594 (1H, d, J=2.80 Hz), 7.495 (1H, dd, J1=9.52 Hz, J2=2.52 Hz), 7.24-7.34 (5H, m), 6.365 (1H, d, J=9.52 Hz), 4.112 (2H, s), 3.891 (2H, s), 3.208 (2H, d, J=13.15 Hz), 3.031 (2H, t, J1=11.20 Hz, J2=12.60 Hz), 1.742 (2H, t×d, J1=11.20 Hz, J2=3.95 Hz), 1.573 (2H, J=14.57 Hz).

Workup

  1. customwere used for preparing a free base

Sources & evidence

ORD record
ord-742294f5d54b447bb32b20c922119df3
Source dataset
uspto-grants-2014_12
Patent number
US08921563B2

Reaction notes

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