Hydrochloric Acid → 4-(5-Bromoindolin-1-yl)cyclohexanone

HRID 1922515Notes

Reaction equation

HRID 1922515 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]1)[CH2:6][CH2:5]2.Cl>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]1)[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 585053135-Bromo-1-(1,4-dioxaspiro[4.5]decan-8-yl)indoline

Product 1

HCID 598070744-(5-Bromoindolin-1-yl)cyclohexanoneYield 83.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 4 (4.0 g, 11.83 mmol) in acetone (50 mL) was treated with 10% HCl solution (50 mL) and the resulting mixture was stirred for over night (16 h). Acetone was evaporated, crude was basified with 2 N NaOH solution and product was extracted into CH2Cl2 (3×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and the crude product was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:4) to obtain compound 5 (2.9 g, 83%) as a solid. 1H NMR (CDCl3) δ 7.15 (d, J=6.6 Hz, 2H), 6.32 (d, J=8.7 Hz, 1H), 3.81 (tt, J=7.2, 23.4 Hz, 1H), 3.37 (t, J=16.8 Hz, 2H), 2.95 (t, J=16.5 Hz, 2H), 2.51-2.41 (m, 4H), 2.18-2.11 (m, 2H), 1.92-1.78 (m, 2H). MS-ESI (m/z, %): 296 (96), 294 (M+, 100), 200 (30).

Workup

  1. customAcetone was evaporated
  2. extractionwas extracted into CH2Cl2 (3×25 mL)
  3. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude product was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:4)

Sources & evidence

ORD record
ord-dc6c85701d9e4229b65649a5c22abca5
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…