Hydrochloric Acid → HCID 67462319, compound

HRID 1908006Notes

Reaction equation

HRID 1908006 reaction equation
[CH2:1]([O:3][CH:4](OCC)[CH:5]1[C:14]2([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[O:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:27])[CH3:2].[ClH:31]>C1(C)C=CC=CC=1>[ClH:31].[CH2:1]([O:3]/[CH:4]=[C:5]1\[C:6](=[O:27])[C:7]2[C:12]([O:13][C:14]3\1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58550808HCID 58550808, compound

Product 1

HCID 67462319HCID 67462319, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To tert-butyl 3-(diethoxymethyl)-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylate (33.0 g, 78.7 mmol) in toluene (73.33 mL) was added hydrochloric acid (68.8 mL of 4.0 M in dioxane, 275 mmol). The reaction mixture was heated at 60° C. for 15 min. Most of the solvent was removed under vacuum, and the tan slurry was filtered using a medium frit. The solids were washed with 500 mL of toluene. The solids were dried to give (Z)-3-(ethoxymethylene)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (15.4 g, 63%). ESI-MS m/z calc. 273.1. found 274.3 (M+1)+; Retention time: 0.85 minutes (3 min run).

Workup

  1. customMost of the solvent was removed under vacuum
  2. filtrationthe tan slurry was filtered
  3. washThe solids were washed with 500 mL of toluene
  4. customThe solids were dried

Sources & evidence

ORD record
ord-d9492d29c00d45a0889754da2b0c552a
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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