Hydrochloric Acid → HCID 67462319, compound

HRID 2204092Notes

Reaction equation

HRID 2204092 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-57e17c1eec6e4962a4740cb3c3a9fc77
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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