Hydrazine → HCID 12417948, compound

HRID 1406675Notes

Reaction equation

HRID 1406675 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([O:16]CC)=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][NH2:20]>C(O)C>[C:1]1([N:7]2[CH2:8][CH2:9][N:10]([CH2:13][C:14]([NH:19][NH2:20])=[O:16])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 30442591-Piperazineacetic acid, 4-phenyl-, ethyl ester

Product 1

HCID 12417948HCID 12417948, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{30} (1.23 g, 6.06 mmol, 1 equiv.), anhydrous hydrazine (0.96 mL, 18.2 mmol, 3 equiv.), ethanol (12.1 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{30} (1.23 g, 87%) as a yellow oil. 1H-NMR (500 MHz, CDCl3): δ 8.20 (br s, 1H), 7.29-7.26 (m, 2H), 6.92 (d, 2H, J=8.0 Hz), 6.88 (t, 1H, J=7.0 Hz), 3.51 (br s, 2H), 3.20 (t, 4H, J=5.0 Hz), 3.16 (s, 2H), 2.70 (t, 4H, J=5.0 Hz), 1.23 (t, 3H, J=7.0 Hz). 13C-NMR (125 MHz, CDCl3): δ 170.2, 150.9, 129.1, 120.0, 116.1, 60.5, 53.6, 49.2.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{30} (1.23 g, 87%) as a yellow oil

Sources & evidence

ORD record
ord-e5f297a112d24568b2c4eb5307700b91
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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