Hydrogen Bromide → α-(1,1-Dimethylethyl)-2-pyridinemethanamine

HRID 1623999Notes

Reaction equation

HRID 1623999 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[C@H:3]([NH:10]C(=O)[C@](OC)(C1C=CC=CC=1)C(F)(F)F)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.CC(C)(C)[C@@H](NC(=O)[C@](OC)(C1C=CC=CC=1)C(F)(F)F)C1C=CC=CN=1.Br>O>[CH3:1][C:2]([CH3:27])([CH3:26])[CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[NH2:10]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 67060926HCID 67060926, compoundHCID 68182409HCID 68182409, compound

Product 1

HCID 12294448α-(1,1-Dimethylethyl)-2-pyridinemethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solutions of (R)—N—((S)-2,2-dimethyl-1-(pyridin-2-yl)propyl)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamide (0.56 g, 1.472 mmol) or (R)—N—((R)-2,2-dimethyl-1-(pyridin-2-yl)propyl)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamide (0.56 g, 1.472 mmol) in 48 wt % aqueous hydrogen bromide (5.02 mL, 44.2 mmol) were heated under microwave irradiation at 160° C. for 2 h. The mixtures were diluted with water (25 mL), extracted with dichloromethane (3×25 mL), and the dichloromethane extracts discarded. The aqueous solutions were basified with 2 M aqueous NaOH (25 mL) then extracted with dichloromethane (3×25 mL). These extracts were dried (MgSO4), filtered, then concentrated to give enantiomeric 2,2-dimethyl-1-(pyridin-2-yl)propan-1-amine derived from first-eluting diastereomer (0.175 g) and enantiomeric 2,2-dimethyl-1-(pyridin-2-yl)propan-1-amine derived from second-eluting diastereomer (0.200 g) as yellow oils.

Workup

  1. extractionextracted with dichloromethane (3×25 mL)
  2. extractionthen extracted with dichloromethane (3×25 mL)
  3. dry with materialThese extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd2966c97d224212bb0f17ab95b4f633
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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