Triethylamine → HCID 89816011, compound

HRID 1482959Notes

Reaction equation

HRID 1482959 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:13][CH3:14])[CH:11]=2)[CH:6]=[C:5]1[C:15](=O)[CH:16]([CH3:18])[CH3:17].CCN(CC)CC.[BH4-].[Na+]>CO>[CH:16]([CH:15]1[C:5]2=[CH:6][C:7]3[CH:8]=[CH:9][C:10]([S:13][CH3:14])=[CH:11][C:12]=3[N:4]2[CH2:3][CH2:2][NH:1]1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 89816040HCID 89816040, compound

Product 1

HCID 89816011HCID 89816011, compoundYield 42.46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(1-(2-aminoethyl)-6-(methylthio)-1H-indol-2-yl)-2-methylpropan-1-one (200 mg, 0.724 mmol) in MeOH (5 mL) was added Et3N (219.3 mg, 2.172 mmol). The reaction mixture was stirred at 60° C. for 1 h. Then NaBH4 (82.53 mg, 2.172 mmol) was added to the formed mixture. The mixture was stirred at 60° C. for another 1 h. The mixture was concentrated, treated with water (10 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and purified by preparative TLC on silica gel eluted with PE/EtOAc 1:1 to afford 1-isopropyl-7-(methylthio)-1,2,3,4-tetrahydropyrazino[1,2-a]indole (80 mg, 42.46% yield, store at 0° C.) as a colorless oil. LC-MS of 1-Isopropyl-7-methylsulfanyl-3,4-dihydro-pyrazino[1,2-a]indole MS (ESI) m/z 259.1 [M+H]+. LC-MS of 1-isopropyl-7-(methylthio)-1,2,3,4-tetrahydropyrazino[1,2-a]indole MS (ESI) m/z 261.2 [M+H]+. 1H NMR (CDCl3 400 MHz): δ 7.41 (d, J=8.4 Hz, 1H), 7.20 (s, 1H), 7.05 (dd, J1=8.4 Hz, J2=1.6 Hz, 1H), 6.12 (s, 1H), 4.02-3.97 (m, 2H), 3.86-3.80 (m, 1H), 3.46-3.42 (m, 1H), 3.16-3.10 (m, 1H), 2.48 (s, 3H), 2.32-2.27 (m, 1H), 1.09 (d, J=6.8 Hz, 3H), 0.86 (d, J=6.8 Hz, 3H).

Workup

  1. stirringThe mixture was stirred at 60° C. for another 1 h
  2. concentrationThe mixture was concentrated
  3. additiontreated with water (10 mL)
  4. extractionextracted with EtOAc (20 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by preparative TLC on silica gel
  9. washeluted with PE/EtOAc 1:1

Sources & evidence

ORD record
ord-d2fdda490b494e78adbf235be7a51256
Source dataset
uspto-grants-2016_08
Patent number
US09416135B2

Reaction notes

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