Hydrazine hydrate (1:1) → HCID 86629527, compound

HRID 1711164Notes

Reaction equation

HRID 1711164 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)[C:22]([NH:24][O:25][CH3:26])=[O:23])[CH2:17][CH2:16]1.O.NN>CCO.CCOCC>[NH2:3][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)[C:22]([NH:24][O:25][CH3:26])=[O:23])[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86629526HCID 86629526, compound

Product 1

HCID 86629527HCID 86629527, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-{1-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-piperidin-4-yl}-3-methoxy-1-thiophen-3-ylmethyl-urea (0.69 g, 1.56 mmol) in EtOH (15 ml) was added hydrazine hydrate (0.49 ml, 15.6 mmol) and the reaction was stirred at rt for 16 h. The reaction mixture was diluted with Et2O (40 ml) to give a white precipitate. The solid was removed via suction filtration and the filtrate was concentrated in vacuo to give a white foam. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 83:15:2, v/v/v) gave 1-[1-(3-amino-propyl)-piperidin-4-yl]-3-methoxy-1-thiophen-3-ylmethyl-urea as a white foam (0.280 g, 57%). 1H NMR (CDCl3) δ 1.60-1.72 (m, 6H), 2.00 (t, 2H, J=9.0 Hz), 2.07 (br s, 3H), 2.39 (t, 2H, J=6.0 Hz), 2.75 (t, 2H, J=6.0 Hz), 2.98 (d, 2H, J=12.0 Hz), 3.65 (s, 3H), 4.25 (m, 1H), 4.29 (s, 2H), 6.95 (d, 1H, J=3.0 Hz), 7.10 (s, 2H), 7.34 (m, 1H).

Workup

  1. customto give a white precipitate
  2. customThe solid was removed via suction filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a white foam
  5. customPurification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 83:15:2, v/v/v)

Sources & evidence

ORD record
ord-58a62bb50ebd4c1ca212dfb6446ab4fc
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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