Sodium hydride → HCID 11626285, compound

HRID 1441940Notes

Reaction equation

HRID 1441940 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1>O1CCCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:29](=[O:30])[NH:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([Br:21])[CH:23]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1410013-Bromophenyl isocyanateHCID 68543194HCID 68543194, compound

Product 1

HCID 11626285HCID 11626285, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.239 g., 1 mmol) in dry tetrahydrofuran (5 ml) was added to a stirred suspension of sodium hydride (0.024 g. 1 mmol) in dry tetrahydrofuran (5 ml) at −10° C. during 5 min. The reaction mixture was stirred for 20 min. Then 3-bromo-phenyl isocyanate (0.237 g., 1.2 mmol) was added to the stirring reaction mixture. Stirring was continued for additional 2.5 hours during which the temperature was allowed to rise to room temperature (34° C.). The reaction mixture was quenched with water (0.2 ml), concentrated under vaccum, diluted with water (5 ml), extracted with chloroform (2×5 ml) and dried over sodium sulphate. The combined fractions of chloroform were concentrated under vaccum. The residue was chromatographed on silica gel using chloroform: hexane (20:80) as eluant to give 2j; yield: 0.25 g. (57.2%), m.p. 117° C., C23H21BrN2O2; 1H NMR δ ppm (CDCl3): 2.00-2.20 (m, 2H), 2.81 (t, 2H), 3.36 (t, 2H), 4.46 (s, 21), 6.46 (d, 1H), 6.79-6.81 (m, 2H), 7.19-7.31 (m, 8H), 7.69 (s, 1H); IR vmax (KBr) (cm−1): 621, 670, 759, 885, 930, 1021, 1117, 1215, 1348, 1420, 1505, 1594, 1743, 2369, 2855, 2928, 3021, 3428; MS: m/z=437 (M+).

Workup

  1. stirringStirring
  2. waitwas continued for additional 2.5 hours during which
  3. customto rise to room temperature
  4. custom(34° C.)
  5. customThe reaction mixture was quenched with water (0.2 ml)
  6. concentrationconcentrated under vaccum
  7. additiondiluted with water (5 ml)
  8. extractionextracted with chloroform (2×5 ml)
  9. dry with materialdried over sodium sulphate
  10. concentrationThe combined fractions of chloroform were concentrated under vaccum
  11. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-27e395296c7b41a3b790c911407a61c2
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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