Hydrochloric Acid → HCID 22396675, compound

HRID 1071130Notes

Reaction equation

HRID 1071130 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:10]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17][C:11]=3[NH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1.[ClH:29]>O1CCOCC1>[ClH:29].[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:10]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][C:11]=3[NH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22396883HCID 22396883, compound

Product 1

HCID 22396675HCID 22396675, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The tert-butyl 10-(2-methylphenyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.53 g, 1.40 mmol) from above was treated with a solution of 4 N HCl in dioxane (10 mL) and stirred at room temperature for 3.7 hours. After the reaction mixture was concentrated in vacuo CH2Cl2 was added and the solution was concentrated in vacuo to give a green solid (475 mg) which was recrystallized from CH3OH/ethyl acetate to give 0.362 g (82%) of a light brown solid as the title compound: mp 278.5-281° C. 1H NMR (400 MHz, DMSO-d6) δ 11.20 (s, 1H), 9.40 (br s, 1H), 7.32-7.22 (m, 4H), 7.15 (d, J=7.2 Hz, 1H), 7.09-7.05 (m, 1H), 6.68 (d, J=7.1 Hz, 1H), 3.26 (m, 2H), 3.17-3.16 (m, 2H), 2.98 (m, 2H), 2.37-2.27 (m, 2H), 1.98 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 140.9, 135.8, 135.5, 134.5, 132.7, 129.4, 129.2, 127.2, 125.3, 125.0, 120.2, 119.7, 110.0, 109.7, 45.9, 44.2, 24.3, 21.1, 19.6; IR (diffuse reflectance) 3257 (s), 2992 (s), 2946 (s,b), 2906 (s,b), 2849 (s), 2831 (s), 2801 (s), 2774 (s), 2676, 2572, 2446, 1463, 1336, 766, 744 (s) cm−1; HRMS (FAB) calcd for C19H20N2+H1 277.1704, found 277.1702. Anal. Calcd for C19H20N2.HCl.0.5EtOAc: C, 72.69; H, 6.80; N, 8.83. Found: C, 72.60; H, 6.82; N, 8.94.

Workup

  1. concentrationAfter the reaction mixture was concentrated in vacuo CH2Cl2
  2. additionwas added
  3. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7c5a6ff5a0d846859094419e76bd7676
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

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