1,1-Dimethylethyl 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate → 7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

HRID 1514269Notes

Reaction equation

HRID 1514269 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:34]=[CH:33][C:20]4[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]>Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:34]=[CH:33][C:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 1

HCID 594034491,1-Dimethylethyl 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 684687897-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochlorideYield 163.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1,1-dimethylethyl 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 42) (950 mg, 1.963 mmol) in hydrochloric acid (a 4M solution in dioxane, 10 ml, 40.0 mmol) and 1,4-dioxane (10 ml) was stirred at room temperature for 5 hours (a precipitate had formed). The reaction mixture was filtered and washed with dioxane (˜5 ml), and the solid dried under vacuum (pistol) overnight to yield the title compound (711 mg, 1.607 mmol, 82% yield) as a white solid. δH (CDCl3, 400 MHz): 10.17 (2H, br s), 8.25 (1H, d), 8.06 (1H, dd), 7.98-8.03 (2H, m), 7.33 (1H, d), 7.06 (1H, d), 4.72 (1H, sept), 3.35-3.47 (8H, m), 1.46 (6H, d). MS (ES): C21H2235ClN3O2 requires 383; found 384 [M+H]+.

Workup

  1. customhad formed)
  2. filtrationThe reaction mixture was filtered
  3. washwashed with dioxane (˜5 ml)
  4. customthe solid dried under vacuum (pistol) overnight

Sources & evidence

ORD record
ord-ad0ce36223fa45508f4d07166682112e
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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