1-Ethylpiperazine → HCID 86650117, compound

HRID 2179751Notes

Reaction equation

HRID 2179751 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:17][CH2:16][C@@H:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]2)(=O)=O)=CC=1.[CH2:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[CH3:27]>C(Cl)Cl>[CH2:26]([N:28]1[CH2:33][CH2:32][N:31]([CH2:12][C@H:13]2[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:14]2)[CH2:30][CH2:29]1)[CH3:27]

Participants

4

Reactant 2

HCID 791961-EthylpiperazineHCID 86650113HCID 86650113, compound

Product 1

HCID 86650117HCID 86650117, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ((1S,3R)-3-(tert-butoxycarbonylamino)cyclopentyl)methyl 4-methylbenzenesulfonate (Intermediate 18-step 2, about 0.5 g) in DCM (50 ml) potassium carbonate (about 0.3 g) was added at room temperature and cooled to about 0° C. After ten minutes, 1-ethyl piperazine (0.23 g) was added and stirred the reaction at room temperature for about 6 hours then completion of the reaction monitored by TLC. The reaction mixture was neutralized and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (0.3 g) as a pale yellow solid. 1H NMR (300 MHz, CDCl3: 1.09-1.24 (m, 3H); 1.39 (s, 9H); 2.29-2.60 (m, 4H); 2.79-2.80 (m, 10H); 3.06-3.18 (m, 6H); 3.70-3.73 (m, 1H); ES Mass: 312 (100%) [M+1].

Workup

  1. waitAfter ten minutes
  2. customthe reaction at room temperature for about 6 hours
  3. extractionextracted with DCM
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce54d6db1f094b8dad51255d5aeaf2a3
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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