4-Chlorophenyl Isocyanate → HCID 60163512, compound

HRID 1843289Notes

Reaction equation

HRID 1843289 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.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>O1CCCC1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:35])[O:18][C:15]2[CH:16]=[C:17]3[C:12]([CH2:11][CH2:10][CH2:9][N:8]3[CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:13][CH:14]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 218649361-Benzyl-1,2,3,4-tetrahydroquinolin-7-ol

Product 1

HCID 60163512HCID 60163512, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 1-benzyl-1,2,3,4-tetrahydroquinolin-7-ol (800 mg, 3.34 mM) and triethylamine (1.5 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, 4-chiorophenyl isocyanate (641 mg/ml, 5.01 mM) was added at once and then the reaction mixture was further stirred for 72 hours under N2 atmosphere at 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 crystallized with methanol-ether (1:6) to give 8f as solid. Yield: 1.06 g, 80.70%.

Workup

  1. additionwas added at once and then the reaction mixture
  2. stirringwas further stirred for 72 hours under N2 atmosphere at 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 crystallized with methanol-ether (1:6)

Sources & evidence

ORD record
ord-07b184649a4d4a529bcc033bd9892f5d
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

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