1-Iodopropane → HCID 22396846, compound

HRID 1356342Notes

Reaction equation

HRID 1356342 reaction equation
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[OH:29])=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:31][CH2:32][CH3:33].C(OCC)(=O)C.CCCCCC>CC(C)=O>[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH2:31][CH2:32][CH3:33])=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 21226206Ethyl acetate hexaneHCID 22396867HCID 22396867, compound

Product 1

HCID 22396846HCID 22396846, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A slurry of 2-(3-benzoyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-10-yl)phenol (357 mg, 0.93 mmol), CS2CO3 (1.24 g, 3.82 mmol) and 1-iodopropane (195 mg, 1.15 mmol) in acetone (10 mL) was stirred at room temperature under nitrogen for 15 hours. The reaction was filtered and the filtrate concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to give a yellow oil which was passed through a column of silica gel with 50% ethyl acetate/hexane to give 276 mg (70%) of a white foam as the title compound: MS m/z 425.3 (M++H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil which

Sources & evidence

ORD record
ord-1422bba096274108a0982ede62634c95
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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