Tert-Butylamine → HCID 23388611, compound

HRID 989889Notes

Reaction equation

HRID 989889 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][C:14]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)([C:17]([OH:19])=O)[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[C:32]([NH2:36])([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][C:14]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)([C:17]([NH:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:19])[CH2:13][CH2:12]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 65578Oxalyl chlorideHCID 21936871HCID 21936871, compound

Product 1

HCID 23388611HCID 23388611, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Cyclohexyl-1,4-piperidinedicarboxylic acid 1-(phenylmethyl) ester (8-4) (2.50 g, 7.24 mmol) was dissolved in 36 mL of methylene chloride and cooled at 0° C. in an ice-water bath. Oxalyl chloride (2.0 M solution in CH2Cl2, 3.98 mL, 7.96 mmol) was then added dropwise followed by the addition of 1-2 drops of DMF. This mixture was stirred at 0° C. for 2 h and then concentrated with toluene. The residue was dissolved in 36 mL of methylene chloride and cooled at 0° C. in an ice-water bath. tert-Butylamine (2.28 mL, 21.7 mmol) was then added dropwise, and the reaction mixture was stirred at 0° C. for 2 h, warmed to room temperature, and stirred at room temperature overnight. The resulting mixture was diluted with methylene chloride, washed with brine, dried over MgSO4, filtered, and concentrated to give 2.92 g of title compound 8-5 as a solid. LCMS (ESI): m/z 401 (M++1).

Workup

  1. concentrationconcentrated with toluene
  2. dissolutionThe residue was dissolved in 36 mL of methylene chloride
  3. temperaturecooled at 0° C. in an ice-water bath
  4. stirringthe reaction mixture was stirred at 0° C. for 2 h
  5. temperaturewarmed to room temperature
  6. stirringstirred at room temperature overnight
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bbb90b48a01f42a9aa183f703f5bfd49
Source dataset
uspto-grants-2002_10
Patent number
US06458790B2

Reaction notes

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