Diisopropylethylamine → HCID 68538988, compound

HRID 2358464Notes

Reaction equation

HRID 2358464 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH:8]=[C:7]2[C:18]#[N:19].C([N:23](C(C)C)CC)(C)C.Cl.NO>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH:8]=[C:7]2[C:18]([NH2:23])=[NH:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 68538794HCID 68538794, compound

Product 1

HCID 68538988HCID 68538988, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 7-chloro-1-(tetrahydropyran-4-yl)methyl-1H-indole-3-carbonitrile (12.9 g, 46.9 mmol) in ethanol (280 ml) and di-iso-propylethylamine (16.7 ml, 96.0 mmol) was added hydroxylamine hydrochloride (6.8 g, 121.4 mmol). The reaction mixture was warmed to reflux and stirred for 6 h before cooling to room temperature and the solvent removed in vacuo. The solid was dissolved in dichloromethane washed with water and brine, dried over sodium sulfate and the solvent removed in vacuo. The resulting solid was crystallised from diethyl ether to yield 7-chloro-1-(tetrahydropyran-4-yl)methyl-1H-indole-3-carboxamidine (13.1 g, 42.5 mmol) as an off white solid.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux
  3. customthe solvent removed in vacuo
  4. dissolutionThe solid was dissolved in dichloromethane
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed in vacuo
  8. customThe resulting solid was crystallised from diethyl ether

Sources & evidence

ORD record
ord-81416d21b82e4e1cb5fb110bb2bb7d64
Source dataset
uspto-grants-2010_07
Patent number
US07763732B2

Reaction notes

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