Butylamine → HCID 86627340, compound

HRID 1895980Notes

Reaction equation

HRID 1895980 reaction equation
C(N)CCC.Br[CH:7]=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[CH:21]#[C:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Cu](I)I>[CH:7](=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[C:21]#[C:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 127321-HexyneHCID 45489892tert-Butyl 4-(bromomethylidene)piperidine-1-carboxylate

Product 1

HCID 86627340HCID 86627340, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

A mixture of palladium tetrakis(triphenylphosphine) (21 mg, 0.018 mmol), butylamine (2.5 mL) and Compound 49a (200 mg, 0.724 mmol) were stirred at room temperature for 45 minutes. Copper iodide (10.3 mg, 0.05 mmol) was then added, followed by hex-1-yne (41.6 μL, 0.362 mmol). The solution was heated for 3-5 hours at 70° C. till change in colour to depth blue. The reaction was quenched with ammonium chloride, extracted with diethyl ether, washed with brine, dried over magnesium sulphate, filtered, concentrated to dryness and purified by preparative HPLC-MS e affording the title product (78 mg).

Workup

  1. temperatureThe solution was heated for 3-5 hours at 70° C. till change in colour to depth blue
  2. customThe reaction was quenched with ammonium chloride
  3. extractionextracted with diethyl ether
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. custompurified by preparative HPLC-MS e

Sources & evidence

ORD record
ord-02db806b209e4512a310c3b5f4ceddec
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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