Acetic Acid → HCID 19768347, compound

HRID 1590937Notes

Reaction equation

HRID 1590937 reaction equation
C(O)(=O)C.[CH:5]1([O:11][N:12]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15](=O)[CH2:14][C:13]2([CH3:22])[CH3:21])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH2:23]([NH2:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C([BH3-])#N.[Na+]>O1CCCC1>[CH:5]1([O:11][N:12]2[C:17]([CH3:19])([CH3:18])[CH2:16][CH:15]([NH:35][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:14][C:13]2([CH3:22])[CH3:21])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 13583DodecylamineHCID 5003444Sodium cyanoborohydrideHCID 22019868N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidine

Product 1

HCID 19768347HCID 19768347, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
21 °C

Procedure

Acetic acid (22.0 g, 367 mmol) is added dropwise to a solution of 15.0 g (59.2 mmol) of 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-one and 54.9 g (296 mmol) of dodecylamine in 200 ml of dry tetrahydrofuran containing 5A molecular sieves (25 g). The reaction mixture warms during the addition. The mixture is then diluted with tetrahydrofuran (150 ml) and cooled to 21° C. Sodium cyanoborohydride (4.46 g, 7.1 mmol) is added in one portion. The reaction mixture is stirred at room temperature for 4 hours, then filtered. The filtrate is concentrated and the residue is partitioned between ether (400 ml) and 5% sodium hydroxide (250 ml). The organic layer is dried over magnesium sulfate, filtered, and concentrated. Residual dodecylamine is removed by Kugelrohr distillation (110° C., 0.3 mm). The crude product is purified by chromatography (silica gel) to afford 20.4 g (82% yield) of the title compound, as a nearly colorless oil.

Workup

  1. additionThe reaction mixture warms during the addition
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated
  4. customthe residue is partitioned between ether (400 ml) and 5% sodium hydroxide (250 ml)
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customResidual dodecylamine is removed by Kugelrohr distillation (110° C., 0.3 mm)
  9. customThe crude product is purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-700972352fd14d6c85d4e8e5055c34aa
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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