Methanol → 2-[(9-Benzyl-6-methoxy-9H-carbazol-4-yl)oxy]ethylamine

HRID 1057657Notes

Reaction equation

HRID 1057657 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][C:23]#[N:24])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([O:25][CH3:26])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH2:24])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([O:25][CH3:26])[CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 18671663[(9-Benzyl-6-methoxy-9H-carbazol-4-yl)oxy]acetonitrile

Product 1

HCID 98630522-[(9-Benzyl-6-methoxy-9H-carbazol-4-yl)oxy]ethylamineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of [(9-benzyl-6-methoxy-9H-carbazol-4-yl)oxy]acetonitrile (0.43 g, 1.26 mmol) in dry THF (20 mL) is added borane-methylsulfide complex (0.36 mL, 3.8 mmol). The mixture is heated at 85° C. overnight. Methanol is slowly added to the mixture until gas evolution ceased. The solvents are removed under reduced pressure. Methanol (20 mL) is added then removed under reduced pressure. Methanol (50 mL) and concentrated hydrochloric acid (10 mL) is added to the mixture and heated at 65° C. overnight. The mixture is neutralized with saturated potassium carbonate and partitioned between water and CH2Cl2. The layers are separated and the organic layer washed twice with water (100 mL). The CH2Cl2 is dried over anhydrous sodium sulfate and concentrated. Column chromatography with silica gel (60 mL) using 4% CH3OH in CH2Cl2 gave 0.371 g (85%) of the title compound; IR (drift) 1581, 1488, 1467, 1452, 1440, 1343, 1323, 1289, 1271, 1211, 1167, 1150, 1031, 742, 727 cm−1. HRMS (FAB) calcd for C22H22N2O2+H1 347.1759, found 347.1761. % Water (KF): 0.17. 1H NMR (CDCl3) δ3.28, 3.92, 4.28, 5.47, 6.65, 6.95, 7.02, 7.09, 7.21, 7.32, 7.87; Anal. Calcd for C22H22N2O2: C, 76.15; H, 6.41; N, 8.07. Found: C, 75.90; H, 6.38; N, 7.99.

Workup

  1. additionis added borane-methylsulfide complex (0.36 mL, 3.8 mmol)
  2. customThe solvents are removed under reduced pressure
  3. additionMethanol (20 mL) is added
  4. customthen removed under reduced pressure
  5. additionMethanol (50 mL) and concentrated hydrochloric acid (10 mL) is added to the mixture
  6. temperatureheated at 65° C. overnight
  7. custompartitioned between water and CH2Cl2
  8. customThe layers are separated
  9. washthe organic layer washed twice with water (100 mL)
  10. dry with materialThe CH2Cl2 is dried over anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7b3d032e474d4e4090e29fc97e0481ce
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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