Sodium hydride → HCID 11694964, compound

HRID 1441943Notes

Reaction equation

HRID 1441943 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[CH2:15]([N:21]=[C:22]=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>O1CCCC1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:22](=[O:23])[NH:21][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75659Hexyl isocyanateHCID 22755149HCID 22755149, compound

Product 1

HCID 11694964HCID 11694964, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.244 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 hexyl isocyanate (0.26 g., 1 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 2m; yield: 0.25 g. (57.9%), m.p. 50° C., C17H26N2O2; 1H NMR δ ppm (CDCl3): 0.88 (bs, 3H), 1.26-1.54 (m, 8H), 1.96-1.99 (m, 2H), 2.71 (t, 2H), 2.85 (s, 3H), 3.14-3.25 (m, 4H), 4.90 (bs, 1H), 6.54 (d, 1H), 6.71-6.87 (m, 2H); IR vmax (KBr) (cm−1): 656, 757, 895, 1160, 1226, 1319, 1387, 1502, 1721, 2932, 1914, 2370, 2863, 3339, 3773; MS: m/z: 391 (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-158fe82aec824e4c8fee83fc547883ee
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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