Tert-Butylamine → HCID 89422940, compound

HRID 1481680Notes

Reaction equation

HRID 1481680 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=O)[CH2:13][CH2:14][CH3:15])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[CH3:17][C:18]([NH2:21])([CH3:20])[CH3:19]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:17][C:18]([N:21]=[C:12]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]2)[CH2:13][CH2:14][CH3:15])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 39104401HCID 39104401, compound

Product 1

HCID 89422940HCID 89422940, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)butan-1-one (2.94 g, 13.5 mmol) in CH2Cl2 (14 mL) was added 2-methylpropan-2-amine (5.7 mL, 54.2 mmol, 4.0 eq). The mixture was cooled to 0° C. before TiCl4 (1.0M in CH2Cl2, 8.8 mL, 8.8 mmol, 0.65 eq) was added via syringe pump over 30 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL) then extracted by CH2Cl2 (5×25 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was carried over to next step without further purification. LC-MS 273.1 [M+H]+, RT 0.65 min. (1 min Method).

Workup

  1. additionwas added via syringe pump over 30 min
  2. customThe reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL)
  3. extractionthen extracted by CH2Cl2 (5×25 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-9b2bb029956d44299353139e2611a6a5
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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