1,4-Dioxane → HCID 58551180, compound

HRID 1907982Notes

Reaction equation

HRID 1907982 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]2[N:7]3[CH:25]=[CH:24][CH:23]=[C:8]3[C:9]3([CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[O:10][C:5]=2[CH:4]=1)#[N:2].O1CCOCC1>Cl>[NH:13]1[CH2:14][CH2:15][C:9]2([O:10][C:5]3[CH:4]=[C:3]([C:1]#[N:2])[CH:27]=[CH:26][C:6]=3[N:7]3[CH:25]=[CH:24][CH:23]=[C:8]23)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 58550825HCID 58550825, compound

Product 1

HCID 58551180HCID 58551180, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl 7′-cyanospiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (1.1 g, 3.1 mmol) in HCl in dioxane (3.1 mL of 4.0 M, 12 mmol) was stirred at room temperature for 1 hour. The reaction mixture was evaporated to dryness to yield spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-7-carbonitrile (880 mg, 94%). ESI-MS m/z calc. 265.3. found 266.1 (M+1)+. Retention time: 0.92 minutes (3 min run).

Workup

  1. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-7c80785440ed48d08b13a558ddfb03dc
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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