Hexanal → HCID 68501164, compound

HRID 1711988Notes

Reaction equation

HRID 1711988 reaction equation
C(N(CC)CC)C.O.Cl.[NH:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19].[CH:23](=O)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>[Cu]Br>[CH3:17][Si:18]([CH3:20])([CH3:19])[C:21]#[C:22][CH:23]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 6184HexanalHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 2723901Piperonylamine

Product 1

HCID 68501164HCID 68501164, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Procedure

A 10 ml schlenk tube was charged with copper (I) bromide (3.6 mg, 0.025 mmol), (R,Rax)-[4-(2-diphenylphosphanyl-naphthalen-1-yl)-phthalazin-1-yl]-(1-phenylethyl)amine (15.7 mg, 0.028 mmol) and 4 Å molecular sieves (powdered, 0.25 g) and then purged with argon for 5 min. Dichloromethane (1 ml) was added and the resulting suspension was stirred for 60 min. To the reaction mixture were added triethylamine (56 mg, 0.55 mmol), 4-piperidone monohydrochloride monohydrate (powder, 154 mg, 1.0 mmol), (trimethylsilyl)acetylene (98 mg, 1.00 mmol) and n-hexanal (50 mg, 0.50 mmol). The flask was rinsed with an additional 1 ml of dichloromethane and then sealed. The reaction mixture was stirred vigorously at 23° C. for 22 hrs. The reaction mixture was directly purified by flash chromatography on silica gel (hexane/EtOAc=9:1) to give 102 mg of the title compound as a colorless oil. (Yield: 73%)

Workup

  1. custompurged with argon for 5 min
  2. additionDichloromethane (1 ml) was added
  3. washThe flask was rinsed with an additional 1 ml of dichloromethane
  4. customsealed
  5. stirringThe reaction mixture was stirred vigorously at 23° C. for 22 hrs
  6. customThe reaction mixture was directly purified by flash chromatography on silica gel (hexane/EtOAc=9:1)

Sources & evidence

ORD record
ord-d1a871c4a7cd4eb8b2f6e6505c91c2df
Source dataset
uspto-grants-2010_09
Patent number
US07790882B2

Reaction notes

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