Triethylamine → HCID 86687859, compound

HRID 535907Notes

Reaction equation

HRID 535907 reaction equation
Cl[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH2:12]([OH:18])[CH2:13][CH2:14][CH2:15][C:16]#[CH:17].[C:19]([N:26]1CCC(N)C[CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])C>C1COCC1.CN(C1C=CN=CC=1)C.O.C(OCC)(=O)C>[C:22]([O:21][C:19]([NH:26][CH:27]1[CH2:37][CH2:36][N:35]([CH2:2][C:3]2[CH:11]=[CH:10][C:6]([C:7]([O:18][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17])=[O:8])=[CH:5][CH:4]=2)[CH2:38][CH2:39]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 702345-Hexyn-1-olHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 86687859HCID 86687859, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(chloromethyl)benzoyl chloride (2.00 g; 10.6 mmol) in THF (30 ml) are added 5-hexyn-1-ol (1.18 ml; 10.6 mmol) and DMAP (0.1 g; 0.82 mmol). The mixture is refluxed overnight with stirring. BOC-4-aminopiperidine (2.33 g; 11.6 mmol) and triethylamine (3.24 ml; 23.3 mmol) are added and the mixture is refluxed for further 3 h. Ethyl acetate (200 ml) and water (50 ml) are added. The organic layer is separated, washed with water and with brine and evaporated to dryness. The residue is purified by silica gel column chromatography (gradient cyclohexane/ethyl acetate 8:2→2:8) to yield 5-Hexyn-1-yl 4-[(4-{[(tertbutoxy)carbonyl]amino}piperidin-1-yl)methyl]-benzoate.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. temperaturethe mixture is refluxed for further 3 h
  3. customThe organic layer is separated
  4. washwashed with water and with brine
  5. customevaporated to dryness
  6. customThe residue is purified by silica gel column chromatography (gradient cyclohexane/ethyl acetate 8:2→2:8)

Sources & evidence

ORD record
ord-5aa7b02a1c884fe8844357a2db821a01
Source dataset
uspto-grants-2014_10
Patent number
US08859559B2

Reaction notes

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