HCID 59258500, compound → 1'-(piperidin-4-yl)spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one

HRID 641190Notes

Reaction equation

HRID 641190 reaction equation
[O:1]=[C:2]1[NH:25][C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[C:4]2([CH2:9][CH2:8][N:7]([CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[CH2:6][CH2:5]2)[O:3]1>Cl>[NH:13]1[CH2:14][CH2:15][CH:10]([N:7]2[CH2:8][CH2:9][C:4]3([O:3][C:2](=[O:1])[NH:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]3=4)[CH2:5][CH2:6]2)[CH2:11][CH2:12]1

Participants

3

Reactant 1

HCID 59258500HCID 59258500, compound

Product 1

HCID 250609561'-(piperidin-4-yl)spiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

tert-Butyl 4-(2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4′-piperidine]-1′-yl)piperidine-1-carboxylate (vib) (432 mg, 1.08 mmol) was dissolved in 3.0 N methanolic HCl (10 mL) and stirred at room temperature for 18 hours. Additional 3.0 N methanolic HCl was added (10 mL) and the reaction heated at 60° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, treated with acetonitrile (approx. 25 mL) and re-concentrated to afford 1′-(piperidin-4-yl)spiro[benzo[d][1,3]oxazine-4,4′-piperidin]-2(1H)-one (compound no. 49) bis-hydrochloride as a crystalline white solid. LC/MS m/z 302.0 [M+H]+, retention time 0.34 min (RP-C18, 10-99% CH3CN/0.05% TFA).

Workup

  1. temperaturethe reaction heated at 60° C. for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiontreated with acetonitrile (approx. 25 mL)
  4. concentrationre-concentrated

Sources & evidence

ORD record
ord-a091f99680594aedac35852f7967dc98
Source dataset
uspto-grants-2010_04
Patent number
US07696201B2

Reaction notes

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