Hydrochloric Acid → 2-Phenylsulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

HRID 2036681Notes

Reaction equation

HRID 2036681 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[N:15]([CH3:19])[C:14]4[CH2:20][CH:21]5[NH:25][CH:24]([C:13]=4[C:12]=3[C:11]=2C(OC(C)(C)C)=O)[CH2:23][CH2:22]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:33]CCl.Cl>CO.C(OCC)C>[ClH:33].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14]2[CH2:20][CH:21]4[NH:25][CH:24]([C:13]3=2)[CH2:23][CH2:22]4)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 67085547Tert-butyl 2-phenylsulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 529129722-Phenylsulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochlorideYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

The product from step C (1.22 g, 2.7 mmol) was dissolved in methanol (7 mL) and dichloromethane (5 mL) and 2N HCl in diethylether (70 mL) was added. The reaction was stirred at room temperature for 12 h, after which a precipitate formed. The mixture was diluted with diethylether and filtered providing 2-phenylsulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (900 mg, 86%) as an off-white solid: Mpt 238-244° C. (dec.); 1H NMR (300 MHz, d6-DMSO) δ 9.69 (brs, 1H), 9.15 (brs, 1H), 8.38 (s, 1H), 7.92 (dd, J=8.0, 1.7 Hz, 2H), 7.60 (m, 5H), 5.36 (d, J=4.8 Hz, 1H), 4.47 (brs, 1H), 3.68 (s, 3H), 3.34 (dd, 1H, partially masked by solvent), 3.00 (d, J=17.2 Hz, 1H), 2.25 (m, 2H), 2.08 (t, J=9.6 Hz, 1H), 1.80 (m, 1H); ESI MS m/z 353 [M+H]+; HPLC (Method A)>99% (AUC), tR=12.02 min.

Workup

  1. customafter which a precipitate formed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f76742101aeb4cb787b1afa14e5424cb
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

Loading…