Isopropylamine → HCID 90023267, compound

HRID 711293Notes

Reaction equation

HRID 711293 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Br[CH2:6][C:7]1[CH:8]=[C:9]([B:13]2[O:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][O:14]2)[CH:10]=[CH:11][CH:12]=1>ClCCl>[CH3:19][C:16]1([CH3:20])[CH2:15][O:14][B:13]([C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[CH2:6][NH:4][CH:1]([CH3:3])[CH3:2])[O:18][CH2:17]1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 38449612-[3-(bromomethyl)phenyl]-5,5-dimethyl-1,3,2-dioxaborinane

Product 1

HCID 90023267HCID 90023267, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of isopropylamine (15 mL, 10 g, 180 mmol, 10 eq) in dichloromethane (100 mL) was added dropwise a suspension of 2-[3-(bromomethyl)phenyl]-5,5-dimethyl-1,3,2-dioxaborinane (5.0 g, 18 mmol, 1.0 eq) in dichloromethane (75 mL) over 1 hour. After the addition was complete the reaction was stirred for an additional hour at 23° C. and then the reaction solution was washed with brine, dried over sodium sulfate and concentrated to yield N-[3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzyl]propan-2-amine (4.2 g, 91%) as a clear oil. LRMS m/z (M+H) 516.2 found, 262.2 required.

Workup

  1. additionAfter the addition
  2. washthe reaction solution was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c0ab2823def8460e8cfa214ac31e753d
Source dataset
uspto-grants-2015_11
Patent number
US09181261B2

Reaction notes

Loading…