Triethylamine → HCID 10672818, compound

HRID 1648337Notes

Reaction equation

HRID 1648337 reaction equation
Br[C:2]1(Br)[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])=[CH:8][CH:9]=2)[O:4][CH2:3]1.[OH:25][C:26]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(CC)CC)C>CC#N>[OH:25][C:26]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][N:29]([C:2]2[C:11](=[O:12])[C:10]3[C:5](=[CH:6][C:7]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])=[CH:8][CH:9]=3)[O:4][CH:3]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 963874-Phenylpiperidin-4-olHCID 10600708HCID 10600708, compound

Product 1

HCID 10672818HCID 10672818, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,3-Dibromo-7-(triisopropylsilyloxy)-4-chromanone (5.0 g, 10.5 mmol) was dissolved in CH3CN (150 ml) and 4-hydroxy-4-phenylpiperidine (2.2 g, 12.5 mmol) and triethylamine (2.9 ml, 20.8 mmol) were added. The mixture was stirred overnight at ambient temperature, then concentrated and the residue partitioned between ethyl acetate and water. The organic layer was washed with water (2×50 ml) and brine, dried over CaSO4, concentrated, and the residue chromatographed on silica gel, using gradient elution with ethyl acetate/hexane to yield title product as a white solid (2.3 g, 54%). A portion was recrystallized from ethanol/ether; mp 163°-163.5° C.; IR (KBr) 3437, 2950, 2870, 1635, 1615, 1600, 1447, 1285, 1247, 1200, 1185, 703, 690. Anal. Calcd. for C29H39NO4Si: C, 70.55; H, 7.96; N, 2.84. Found: C, 70.44; H, 7.76; N, 2.84.

Workup

  1. concentrationconcentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water (2×50 ml) and brine
  4. dry with materialdried over CaSO4
  5. concentrationconcentrated
  6. customthe residue chromatographed on silica gel
  7. washelution with ethyl acetate/hexane

Sources & evidence

ORD record
ord-fde703b06e394928ae78ce56e7058981
Source dataset
uspto-grants-1995_07
Patent number
US05436255

Reaction notes

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