Hydrochloric Acid → 2-(4-Aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole dihydrochloride

HRID 2036691Notes

Reaction equation

HRID 2036691 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[ClH:35]>C(OCC)C>[ClH:35].[ClH:35].[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]2[CH2:22][CH:23]4[NH:27][CH:26]([C:15]3=2)[CH2:25][CH2:24]4)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085186Tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 529130972-(4-Aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole dihydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of step A was subjected to Boc-deprotection with 2 M HCl in diethyl ether following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide). The free base was treated with 1.25 M HCl in methanol (0.5 mL). The solution was concentrated in vacuo and the residue lyophilized to give 2-(4-Aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole dihydrochloride (13 mg, 76%, AUC HPLC 97.0%) as an off-white solid: mp 237-239° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.72 (br s, 1H), 9.26 (br s, 1H), 8.50 (br s, 3H), 8.38 (s, 1H), 7.97 (d, J=8.1 Hz, 2H), 7.58-7.74 (m, 4H), 5.34 (br s, 1H), 4.46 (br s, 1H), 4.07 (br s, 2H), 3.67 (s, 3H), 3.39-3.46 (m, 1H), 3.00 (d, J=17.4 Hz, 1H), 2.19-2.39 (m, 2H), 2.04-2.15 (m, 1H), 1.71-1.88 (m, 1H); ESI MS m/z 382 [M+H]+.

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide)
  2. additionThe free base was treated with 1.25 M HCl in methanol (0.5 mL)
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-0fd057100d424a60a5df3d0ed20d0880
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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