Tert-Butylamine → HCID 89422917, compound

HRID 1481765Notes

Reaction equation

HRID 1481765 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([C:18](=O)[CH2:19][CH2:20][CH3:21])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25]>ClCCCl.C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:17]([C:18](=[N:28][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:19][CH2:20][CH3:21])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 6385Tert-ButylamineHCID 71285294HCID 71285294, compound

Product 1

HCID 89422917HCID 89422917, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)butan-1-one (0.260 g, 0.85 mmol) in DCE (4 mL) was added t-BuNH2 (0.40 mL, 3.79 mmol). The mixture was cooled to 0° C. before TiCl4 solution (1M DCE, 0.55 mL, 0.55 mmol) was added dropwise via syringe pump over 30 min. The reaction was allowed to warm to room temperature and then heated at 50° C. for 6 h. The mixture was then diluted with DCM (15 mL) and quenched with NaHCO3 (aqueous saturated, 5 mL). Upon vigorous shaking, the organic phase was separated using a PTFE phase separator and dried over Na2SO4. Removal of the solvent afforded N-(1-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)butylidene)-2-methylpropan-2-amine as a yellow oil, which was taken directly into next step without purification.

Workup

  1. additionwas added dropwise via syringe pump over 30 min
  2. temperatureheated at 50° C. for 6 h
  3. customquenched with NaHCO3 (aqueous saturated, 5 mL)
  4. customUpon vigorous shaking, the organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-33bd5d5582044642842349e58baf32b9
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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