Hydrochloric Acid → HCID 67085200, compound

HRID 2036755Notes

Reaction equation

HRID 2036755 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][CH2:20][OH:21])[C:14]2[CH2:22][CH:23]4[NH:27][CH:26]([C:13]3=2)[CH2:25][CH2:24]4)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:28]>CO>[ClH:28].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][CH2:20][OH:21])[C:14]2[CH2:22][CH:23]4[NH:27][CH:26]([C:13]3=2)[CH2:25][CH2:24]4)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58258845HCID 58258845, compound

Product 1

HCID 67085200HCID 67085200, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of step B (100 mg, 0.26 mmol) was treated with 1.25 M HCl in methanol (2 mL). The solution was concentrated in vacuo and lyophilized from water to give 2-phenylsulfonyl-5-(2-hydroxy)ethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (90 mg, 74%, AUC HPLC >99%) as a white solid: mp 185-190° C.; 1H NMR (CD3OD, 300 MHz) δ 8.26 (s, 1H), 7.93-7.96 (m, 2H), 7.71 (dd, J=8.8, 1.8 Hz, 1H), 7.51-7.62 (m, 4H), 5.25-5.26 (m, 1H), 4.49 (br s, 1H), 4.24 (t, J=5.1 Hz, 2H), 3.80 (t, J=5.1 Hz, 2H), 3.48-3.53 (m, 1H), 3.10 (d, J=18.0 Hz, 1H), 2.23-2.44 (m, 3H), 1.91-1.96 (m, 1H); ESI, m/z 383 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-02e95398f7fe43f18ad91b8118ea6e30
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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