Triethylamine → HCID 60163507, compound

HRID 1843290Notes

Reaction equation

HRID 1843290 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:26]([N:32]=[C:33]=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1>[CH2:26]([NH:32][C:33](=[O:34])[O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH2:9][N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:14]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75659Hexyl isocyanateHCID 218649361-Benzyl-1,2,3,4-tetrahydroquinolin-7-ol

Product 1

HCID 60163507HCID 60163507, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 1-benzyl-1,2,3,4-tetrahydroquinolin-7-ol (500 mg, 2.09 mM) and triethylamine (0.4 mL) in dry tetrahydrofuran (THF, 5 ml) was stirred for half an hour under nitrogen atmosphere at room temperature (35° C.). To the stirred reaction mixture, n-hexyl isocyanate (457 mg/ml, 3.14 mM) was added at once and then the reaction mixture was further stirred for 72 hours under N2 atmosphere a RT. The reaction mixture was concentrated under vacuum and then was added distilled water (15 ml) followed by the extraction with ether (3×15 mL). The ether layer was dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was finally chromatographed using chloroform-hexane (1:9) to give 8g as solid. Yield: 0.619 g, 81%.

Workup

  1. additionwas added at once and then the reaction mixture
  2. stirringwas further stirred for 72 hours under N2 atmosphere a RT
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionwas added
  5. distillationdistilled water (15 ml)
  6. extractionfollowed by the extraction with ether (3×15 mL)
  7. dry with materialThe ether layer was dried over sodium sulphate
  8. concentrationconcentrated under vacuum
  9. customto afford the crude product, which
  10. customwas finally chromatographed

Sources & evidence

ORD record
ord-f2bbd34472844bcbb385e5cecf3180e4
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

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