Hydrochloric Acid → HCID 69436101, compound

HRID 916874Notes

Reaction equation

HRID 916874 reaction equation
[F:1][C:2]1[C:7]2[CH2:8][O:9][CH:10]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:24][CH:23]=3)[C:11]3[C:12](=[CH:13][CH:14]=[C:15]4[C:20]=3[CH:19]=[CH:18][C:17]([OH:21])=[CH:16]4)[C:6]=2[CH:5]=[C:4]([F:37])[C:3]=1[Si](C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[ClH:61].CCOCC>C(#N)C>[ClH:61].[F:1][C:2]1[C:7]2[CH2:8][O:9][CH:10]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]4[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]4)=[CH:24][CH:23]=3)[C:11]3[C:12](=[CH:13][CH:14]=[C:15]4[C:20]=3[CH:19]=[CH:18][C:17]([OH:21])=[CH:16]4)[C:6]=2[CH:5]=[C:4]([F:37])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 58961537HCID 58961537, compound

Product 1

HCID 69436101HCID 69436101, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 1,3-difluoro-11-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-2-trimethylsilanyl-11,13-dihydro-12-oxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-8-ol (2.2 g, 3.8 mmol) in acetonitrile (100 mL) and add tetrabutylammonium fluoride hydrate (2.0 g, 7.6 mmol) and heat to 70° C. for 4 hours. Cool the reaction to room temperature and partition between water and ethyl acetate. Extract the organic layer with water three times. Dry with sodium sulfate, filter and concentrate in vacuo. Dissolve the residue in methylene chloride (8 mL) and add HCl (2M in ether, 3.8 mL, 7.6 mmol). Add the solution slowly to vigorously stirred ether and collect the precipitate. Dry at 50° C. under vacuum over night to yield 1.9 g (93%) of the title compound as a tan solid. 1H NMR (d6-DMSO) δ10.09 (s, 1H), 10.02 (bs, 1H), 8.36 (d, J=9.2 Hz, 1H), 7.92 (d, J=8.6 Hz, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.31 (d, J=2.5 Hz, 1H), 7.22 (dd, J=9.4, 2.7 Hz, 1H), 7.13 (td, J=9.6, 2.3 Hz, 1H), 6.99 (m, 2H), 6.64 (m, 4H), 4.97 (d, J=12.3 Hz, 1H), 4.19 (t, J=5.2 Hz, 2H), 4.07 (d, J=12.3 Hz, 1H), 3.37 (m, 4H), 2.91 (m, 2H), 1.70 (m, 5H), 1.57 (m, 1H). mass spectrum (apci) m/z-502.3 (M−HCl+H). HPLC (5 to 95) Rt (purity at 254 nm)=2.76 min (>99%). Analysis calculated for C31H30ClF2NO3.H2O: C, 66.96; H, 5.80; N, 2.52. Found: C, 67.00; H, 6.20; N, 2.83.

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. custompartition between water and ethyl acetate
  4. extractionExtract the organic layer with water three times
  5. dry with materialDry with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. dissolutionDissolve the residue in methylene chloride (8 mL)
  9. customcollect the precipitate
  10. customDry at 50° C. under vacuum over night

Sources & evidence

ORD record
ord-8e7603e5d5cc4f74ab60be9c57643582
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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