Triethylamine → n-[2-[2-(1,1-Dimethyl-2-propenyl)-1h-indol-3-yl]ethyl]-carbamic acid phenylmethyl ester

HRID 2306974Notes

Reaction equation

HRID 2306974 reaction equation
[CH3:1][C:2]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][NH2:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:5])[CH:3]=[CH2:4].CCN(CC)CC.[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[C:26]1([CH2:25][O:32][C:33](=[O:34])[NH:17][CH2:16][CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:2]([CH3:1])([CH3:5])[CH:3]=[CH2:4])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 223967402-(1,1-dimethyl-2-propenyl)-1H-indole-3-ethanamine

Product 1

HCID 69792966n-[2-[2-(1,1-Dimethyl-2-propenyl)-1h-indol-3-yl]ethyl]-carbamic acid phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(1,1-dimethyl-2-propenyl)-1H-indole-3-ethanamine (0.707 g, 3.07 mmol) in dry CH2Cl2 (30 mL) at 0° C. under argon was added NEt3 (0.98 mL, 6.93 mmol) and BnOC(O)Cl (1.10 mL, 7.32 mmol). The reaction was permitted to warm to rt while stirring overnight. It was diluted with CH2Cl2, and extracted with cold H2O. The CH2Cl2 layer was separated. The H2O layer was re-extracted with CH2Cl2. The combined CH2Cl2 extracts were washed with satd aq NaHCO3 and brine, dried, filtered and concentrated to give an oil. This oil was purified by silica chromatography to provide the title compound: TLC Rf=0.34 (CH2Cl2); MS (EI) m/z 362.3, 254, 211, 198, 182. 168, 167, 108, 91, 77, 65, 51; 1H NMR (300 MHz, CDCl3) δ 7.89 (1H), 7.56 (1H), 7.33-7.26 (6H), 7.10 (2H), 6.12 (1H), 5.18-5.12 (2H), 5.12 (2H), 4.87 (1H), 3.47 (2H), 3.07 (2H), 1.53 (6H).

Workup

  1. extractionextracted with cold H2O
  2. customThe CH2Cl2 layer was separated
  3. extractionThe H2O layer was re-extracted with CH2Cl2
  4. washThe combined CH2Cl2 extracts were washed with satd aq NaHCO3 and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil
  9. customThis oil was purified by silica chromatography

Sources & evidence

ORD record
ord-f4ade653e5b84b5ca9a2b12f59344811
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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