Hexahydro-1,4-diazepine → HCID 131716943, compound

HRID 1086450Notes

Reaction equation

HRID 1086450 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([S:15]([Cl:18])(=[O:17])=[O:16])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.[NH:19]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(Cl)Cl>[ClH:18].[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([S:15]([N:19]4[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)(=[O:17])=[O:16])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 19826025HCID 19826025, compound

Product 1

HCID 131716943HCID 131716943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add the product of step 1 (1.0 g, 2.9 mmol) in methylene chloride (10 mL) dropwise over 10 minutes to hexahydro-2H-1,4-diazepine (0.35 g) in methylene chloride (20 mL). Stir for 18 hours. Partition the reaction mixture between ethyl acetate (75 mL) and hydrochloric acid (75 mL, 1N). Separate, and adjust the pH of the aqueous layer to alkaline pH (phenolphthalein indicator) with aqueous sodium hydroxide (1N) forming a heavy precipitate. Extract the reaction mixture with methylene chloride (100 mL), wash with saturated aqueous sodium bicarbonate (100 mL), saturated aqueous sodium chloride (100 mL). Dry (MgSO4), filter and concentrate in vacuo to give the title compound free base (0.87 g) as a light yellow solid. Rf=0.52 (450:45:5 methylene chloride:methanol:acetic acid). Chromatograph the free base (120 mg) on a column of silica gel (300 g, 60 micron particle size) eluting with 1:9 methanol:methylene chloride to give a solid. Dissolve the solid in hydrochloric acid (10 mL) and concentrate to give the title compound (110 mg) as a white solid, as the semihydrate. Calculated for C18H21O2.5N2SBrCl: C, 47.76; H, 4.68; N, 6.18. Observed: C, 47.76; H, 4.39; N, 6.14.

Workup

  1. customPartition the reaction mixture between ethyl acetate (75 mL) and hydrochloric acid (75 mL, 1N)
  2. customSeparate
  3. customforming a heavy precipitate
  4. extractionExtract the reaction mixture with methylene chloride (100 mL)
  5. washwash with saturated aqueous sodium bicarbonate (100 mL), saturated aqueous sodium chloride (100 mL)
  6. dry with materialDry (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-5661cb62956d4479bf681613550bfc9f
Source dataset
uspto-grants-1991_07
Patent number
US05030631

Reaction notes

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