Triethylamine → HCID 59442775, compound

HRID 243568Notes

Reaction equation

HRID 243568 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]([CH2:8][CH3:9])[CH2:6][CH3:7].[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CCN(CC)CC>CO>[CH2:6]([N:5]([CH2:8][CH3:9])[CH2:4][CH2:3][CH2:2][N:13]1[CH2:14][CH2:15][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12]1)[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 669183-Chloropropyl(diethyl)amineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 59442775HCID 59442775, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

3-Chloro-N,N-diethylpropan-1-amine (1.6 g) is added to a mixture of tert-butyl piperazine-1-carboxylate (2.0 g) and NEt3 (1.5 ml) in methanol (30 ml). The mixture is stirred for 6 hours at 70° C. and cooled to room temperature. The solvent is removed under reduced pressure. Satd. aqueous NaHCO3 is added to the crude product and the aqueous layer is extracted with EtOAc (3×). The combined organic layers are dried (Na2SO4) and filtered, and the solvent is removed under reduced pressure to give tert-butyl 4-(3-(diethylamino)propyl)piperazine-1-carboxylate (2.48 g). m/z(+) 300 (M+H+).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent is removed under reduced pressure
  3. additionaqueous NaHCO3 is added to the crude product
  4. extractionthe aqueous layer is extracted with EtOAc (3×)
  5. dry with materialThe combined organic layers are dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-06a35726d0354e64b983d6142291fd8a
Source dataset
uspto-grants-2014_02
Patent number
US08653262B2

Reaction notes

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