O-ethylhydroxylamine hydrochloride → HCID 58089481, compound

HRID 251485Notes

Reaction equation

[C:1]([N:4]1[CH2:25][C:12]2([CH2:17][CH2:16][N:15]([CH:18]3[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].Cl.[CH2:27]([O:29][NH2:30])[CH3:28]>N1C=CC=CC=1>[CH2:27]([O:29][N:30]=[C:21]1[CH2:20][CH2:19][CH:18]([N:15]2[CH2:14][CH2:13][C:12]3([C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:25]3)[CH2:17][CH2:16]2)[CH2:23][CH2:22]1)[CH3:28]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(2-Acetyl-2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-yl)cyclohexanone 6e (100 mg; 0.29 mmol) was dissolved in pyridine (1 mL) and treated with O-ethyl hydroxyamine hydrochloride (34 mg; 0.35 mmol). The vial was sealed and heated to 60° C. for 1 hr. The solvent was evaporated under reduced pressure and the residue was dissolved in DMSO (2 mL) and purified by LC/MS (10-99% CH3CN—H2O gradient, with 0.05% TFA, 9 min) to provide 1-(1′-(4-(ethoxyimino)cyclohexyl)-1H-spiro[isoquinoline-4,4′-piperidine]-2(3H)-yl)ethanone. LC/MS m/z [M+H]+ 384.4 retention time 1.80 min (10-99% CH3CN—H2O gradient, with 0.05% TFA, 5 min). 1H-NMR (400 MHz, CDCl3) δ7.69 (d, J=7.8 Hz, 1H), 7.26 (t, J=7.3 Hz, 1H), 7.19-7.15 (m, 1H), 7.01 (d, J=7.5 Hz, 1H), 4.63 (s, 2H), 4.00 (q, J=7.0 Hz, 2H), 3.79 (dd, J=13.4, 18.1 Hz, 2H), 3.41 (d, J=13.0 Hz, 1H), 3.33 (d, J=9.3 Hz, 2H), 3.17 (m, 2H), 3.04-2.98 (m, 2H), 2.59-2.47 (m, 4H), 2.14 (s, 3H), 1.76-1.69 (m, 6H), 1.21-1.14 (t, J=7 Hz, 3H).

Workup

customThe vial was sealed
customThe solvent was evaporated under reduced pressure
dissolutionthe residue was dissolved in DMSO (2 mL)
custompurified by LC/MS (10-99% CH3CN—H2O gradient, with 0.05% TFA, 9 min)

Sources & evidence

ORD record: ord-c2d2c54b5a014c7fa598c848af8fff47
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863449B2

Reaction notes

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