1,4-Dioxane hydrochloride → 1-(4-Chlorophenyl)-1,4-diazepane

HRID 241337Notes

Reaction equation

HRID 241337 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 669683174-(4-Chloro-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 213638201-(4-Chlorophenyl)-1,4-diazepaneYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 4-(4-Chloro-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3.10 g, 10.0 mmol) was dissolved in methylene chloride (1 mL) and treated with 4 N HCl/dioxane (10 mL, 40 mmol). The solution was stirred at rt for 1 hour. The reaction was concentrated in vacuo. The residue was diluted with saturated aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (3×30 mL). The combined organics were washed with brine, dried over MgSO4, and evaporated to yield 1.00 g (48%) of the title compound. 1H-NMR (CDCl3) δ: 1.90 (2H, m), 2.23 (1H, brs), 2.83 (2H, m), 3.02 (2H, m), 3.54 (4H, m), 6.58 (2H, d, j=9.3 Hz), 7.13 (2H, d, j=9.3 Hz). ESI-MS m/z: 211 (M+1), FAS method rt: 1.04 min.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionThe residue was diluted with saturated aqueous sodium bicarbonate (100 mL)
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-1b9dbceec02e4844bf759c8993eb4090
Source dataset
uspto-grants-2014_02
Patent number
US08648197B2

Reaction notes

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