Sulfuric Acid → 11-Acetamido-2,3,4,5-tetrahydro-11-phenyl-11H-[1,3]diazepino[1,2-a]indole

HRID 2231720Notes

Reaction equation

HRID 2231720 reaction equation
Br.[C:2]1([C:8]2(O)[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]3[CH2:17][CH2:18][CH2:19][CH2:20][N:21]=[C:9]23)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].C(=O)([O-])[O-:31].[Na+].[Na+].[C:36](#[N:38])[CH3:37]>CS(O)(=O)=O.O>[C:36]([NH:38][C:8]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]2[CH2:17][CH2:18][CH2:19][CH2:20][N:21]=[C:9]12)(=[O:31])[CH3:37]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 21285438HCID 21285438, compound

Product 1

HCID 1574478911-Acetamido-2,3,4,5-tetrahydro-11-phenyl-11H-[1,3]diazepino[1,2-a]indole

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 962WaterSolvent

Procedure

A suspension of 2,4,5,11-tetrahydro-11-phenyl-3H-[1,3]diazepino[1,2-a]indol-11-ol hydrobromide (2.89 g)in acetonitrile (16 ml) and methanesulphonic acid (100 drops) was added dropwise over 10 min to stirred sulphuric acid 98% w/w (8 ml) at 50°-60°. After 1/2 hour, the solution was cooled to room temperature, poured into water (200 ml), basified with sodium hyroxide (10 g) and sodium carbonate and extracted with chloroform (2×200 ml). The extracts were dried (MgSO4) and evaporated in vacuo. The brown oil was purified by chromatography (Al2O3 ; ethyl acetate) to give the product free base (0.82 g) as a colourless solid. The hydrochloride was prepared from ether-methanol as a solid (1.06 g), m.p. 285°-290° (dec.).

Workup

  1. additionwas added dropwise over 10 min
  2. extractionextracted with chloroform (2×200 ml)
  3. dry with materialThe extracts were dried (MgSO4)
  4. customevaporated in vacuo
  5. customThe brown oil was purified by chromatography (Al2O3 ; ethyl acetate)

Sources & evidence

ORD record
ord-741f75d364924b9bb56025026908006e
Source dataset
uspto-grants-1988_11
Patent number
US04783455

Reaction notes

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