Hydrochloric Acid → 7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-imine

HRID 1468232Notes

Reaction equation

HRID 1468232 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:23][CH2:22][CH:21]([O:24][CH3:25])[CH2:20][CH2:19]3)[C:9]2=[N:12]S(C(C)(C)C)=O)=[CH:4][CH:3]=1.Cl>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:23][CH2:22][CH:21]([O:24][CH3:25])[CH2:20][CH2:19]3)[C:9]2=[NH:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86706708N-(7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalene]-1'-ylidene)-2-methylpropane-2-sulfinamide2×

Product 1

HCID 867067097'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-imineYield 76%

Procedure

To N-(7′-bromo-4-methoxy-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-naphthalene]-1′-ylidene)-2-methylpropane-2-sulfinamide (Intermediate 13, 0.610 g, 1.43 mmol) under N2 (g) was added HCl (4 M in 1,4-dioxane, 3.58 mL, 14.3 mmol). The mixture was stirred at r.t. for 45 min and was then concentrated. DCM (approx. 2 mL) was added followed by Et2O. A solid formed and was filtered off and washed with Et2O. The solid was dissolved in DCM. NaHCO3 (sat. aq.) was added and the mixture was poured into a phase separator. The organic phase was collected and concentrated to give the title compound (0.35 g, 76% yield): MS (EI) m/z 321 M+.

Workup

  1. concentrationwas then concentrated
  2. additionDCM (approx. 2 mL) was added
  3. customA solid formed
  4. filtrationwas filtered off
  5. washwashed with Et2O
  6. dissolutionThe solid was dissolved in DCM
  7. additionNaHCO3 (sat. aq.) was added
  8. additionthe mixture was poured into a phase separator
  9. customThe organic phase was collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-652ff472bbea48dcad6d6ec9cb6c4aae
Source dataset
uspto-grants-2015_04
Patent number
US09000184B2

Reaction notes

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