Hydrochloric Acid → 7-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine dihydrochloride

HRID 241086Notes

Reaction equation

HRID 241086 reaction equation
CC(OC([N:8]1[C:12]2[CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]4[O:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][C:21]=4[CH:34]=3)[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH3:35])=O)(C)C.C(OCC)C.[ClH:41]>CO.O1CCOCC1>[ClH:41].[ClH:41].[CH3:35][C:9]1[NH:8][C:12]2[CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]4[O:26][CH2:25][CH2:24][NH:23][CH2:22][C:21]=4[CH:34]=3)[CH:15]=[CH:16][C:11]=2[N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59604600tert-butyl 7-(1-(tert-butoxycarbonyl)-2-methyl-1H-benzo[d]imidazol-6-yl)-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate

Product 1

HCID 668202277-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine dihydrochlorideYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl 7-(1-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methyl-1H-benzimidazol-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (13.1 g, 27 mmol) in a mixture of methanol (20 mL) and 4 N hydrogen chloride in dioxane (30 mL) was refluxed for 15 min. After cooling to room temperature ethyl ether (100 mL) was added, and the reaction mixture was concentrated. Another portion of ethyl ether (100 mL) was added, the precipitate was filtered off, washed several times with ethyl ether, and dried to give 7-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine dihydrochloride (8.9 g, 93% yield) as a light beige solid. 1HNMR (400 MHz, CD3OD): 7.93 (s, 1H), 7.86-7.67 (m, 4H), 7.28 (s, 1H), 4.54 (s, 2H), 4.33-4.23 (m, 2H), 3.65-3.54 (m, 2H), 2.91 (s, 3H); MS (EI) for C17H17N3O: 280 (MH+).

Workup

  1. temperaturewas refluxed for 15 min
  2. additionwas added
  3. concentrationthe reaction mixture was concentrated
  4. additionAnother portion of ethyl ether (100 mL) was added
  5. filtrationthe precipitate was filtered off
  6. washwashed several times with ethyl ether
  7. customdried

Sources & evidence

ORD record
ord-7f8a88a01cfe46a2b644120913e932af
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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