Hydrochloric Acid → HCID 57814299, compound

HRID 1809137Notes

Reaction equation

HRID 1809137 reaction equation
[N:1]([CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[Cl:19])[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=[N+]=[N-].ClC1C(Cl)=CC=CC=1C=CC1C=CN=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[K+].Cl>C1COCC1.O>[Cl:19][C:13]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=1[CH:4]([NH2:1])[CH2:5][C:6]1[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 57814296HCID 57814296, compoundHCID 66925267HCID 66925267, compound

Product 1

HCID 57814299HCID 57814299, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (8) (81% pure, 3.82 g, 10.6 mmol) and (9) in THF (30 mL) was added triphenylphosphine (2.86 g, 10.9 mmol) at room temperature. After the solution was stirred for 15 minutes, potassium hydroxide (0.61 g, 10.9 mmol) in water (6 mL) was added. The resulting mixture was stirred at room temperature overnight. The mixture was acidified to pH˜3 with HCl (2M). The aqueous layer was washed numerous times with diethyl ether, and basified to pH>7 with NaOH (2M). The basic layer was extracted with ethyl acetate. The pooled organic layer was dried over magnesium sulfate. The mixture was filtered. Silica gel was added to the filtrate, and the solvent was removed under vacuum. Purification by chromatography on silica gel (2 to 10% methanol in dichloromethane) gave 1-(2,3-dichlorophenyl)-2-(pyridin-4-yl)ethanamine (10) as a solid (1.71 g, 6.48 mmol, 60% yield).

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. washThe aqueous layer was washed numerous times with diethyl ether
  3. extractionThe basic layer was extracted with ethyl acetate
  4. dry with materialThe pooled organic layer was dried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. additionSilica gel was added to the filtrate
  7. customthe solvent was removed under vacuum
  8. customPurification by chromatography on silica gel (2 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8d1b60b1c59b4134bb3f2020c2ca0bc7
Source dataset
uspto-grants-2013_01
Patent number
US08362022B2

Reaction notes

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