1-Piperazinecarboxylic acid, ethyl ester → HCID 63309138, compound

HRID 923650Notes

Reaction equation

HRID 923650 reaction equation
[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17].CCN(CC)CC>C(Cl)Cl>[Cl:12][CH2:13][CH2:14][CH2:15][C:16]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2][CH2:3]1)=[O:17]

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 63309138HCID 63309138, compoundYield 98,914.602%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl piperazine-1-carboxylate (800 mg, 5.06 mmol) was treated with 4-chlorobutanoyl chloride (856 mg, 6.07 mmol) in anhydrous CH2Cl2 (25 mL) containing Et3N (1.54 kg, 15.17 mmol) at 20° C. for 2 h, and then washed with 1 M HCl(aq). The organic phase was dried over MgSO4, and concentrated under reduced pressure to give ethyl 4-(4-chlorobutanoyl)piperazine-1-carboxylate (1.315 kg, 99% yield). C11H19ClN2O3; pale yellow oil; 1H NMR (400 MHz, CDCl3) δ 4.13 (2H, q, J=7.2 Hz), 3.62 (2H, t, J=5.6 Hz), 3.58 (2H, m), 3.46 (6H, m) 2.49 (2H, t, J=6.8 Hz), 2.11 (2H, m), 1.25 (3H, t, J=7.2 Hz); 13C NMR (100 MHz, CDCl3) δ 170.1, 155.1, 61.7, 45.2, 44.8, 43.7 (2×), 41.4, 29.8, 27.8, 14.7; ESI-HRMS calcd for C11H20ClN2O3: 263.1162. found: m/z 263.1175 [M+H]+.

Workup

  1. washwashed with 1 M HCl(aq)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfa2187d57aa4d96b048d70c0720514f
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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