p-Toluenesulfonic acid → 2-Amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 416488Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:11]([CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)(=[O:13])=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].NN.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.C1COCC1>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:11]([CH2:14][CH2:15][NH2:16])(=[O:12])=[O:13])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

2.48 g (6.53 mmol) crude 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide were dissolved in 100 ml ethanol. 65.3 ml (10 equiv.) of a 1M hydrazine-solution in THF and 124 mg (0.1 equiv.) p-toluenesulfonic acid were added. The resulting mixture was stirred at 60° C. for 72 h. The formed precipitate was filtered off. The filtrate was concentrated under reduced pressure. The resulting residue was co-distilled three times with 200 ml DMF to remove the excess hydrazine. Crude 2-amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide was obtained as a colorless oil. Yield: 2.00 g

Workup

filtrationThe formed precipitate was filtered off
concentrationThe filtrate was concentrated under reduced pressure
customto remove the excess hydrazine

Sources & evidence

ORD record: ord-df608e101716485d9bef561550515227
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088925B2

Reaction notes

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