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Hydrochloric Acid → 2-(3-Fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

HRID 2036693
Notes
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Reaction equation

HRID 2036693 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:19]=[CH:18][C:17]3[N:16]([CH3:20])[C:15]4[CH2:21][CH:22]5[NH:26][CH:25]([C:14]=4[C:13]=3[C:12]=2C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[ClH:34]>O1CCOCC1>[ClH:34].[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[CH2:21][CH:22]4[NH:26][CH:25]([C:14]3=2)[CH2:24][CH2:23]4)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085414Tert-butyl 2-(3-fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 529131012-(3-Fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product of step A (105 mg, 0.22 mmol) was treated with a solution of 4 M HCl in dioxane (1.5 mL). After 1.5 h the mixture was concentrated in vacuo and the residue partitioned with saturated sodium bicarbonate solution and chloroform. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 90:9:1 chloroform/methanol/ammonium hydroxide) to give 2-(3-fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (45 mg, 50%, AUC HPLC 98.8%) as a white solid: mp 240-245° C.; 1H NMR (DMSO-d6, 300 MHz) δ 8.20-8.70 (m, 3H), 7.74-7.81 (m, 2H), 7.59-7.71 (m, 3H), 7.45-7.55 (m, 1H), 5.15-5.24 (m, 1H), 4.31-4.43 (m, 1H), 3.66 (s, 3H), 3.21-3.39 (m, 1H), 2.92 (d, J=16.8 Hz, 1H), 2.12-2.29 (m, 2H), 1.96-2.09 (m, 1H), 1.66-1.80 (m, 1H); ESI MS m/z 371 [M+H]+.

Workup

  1. concentrationAfter 1.5 h the mixture was concentrated in vacuo
  2. customthe residue partitioned with saturated sodium bicarbonate solution and chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 90:9:1 chloroform/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-8f2976ddcde646a5aa04d789023efdb1
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575186B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes