Hydrazine → {4-[4-(4-Aminopentyl)phenyl]butyl}carbamic acid benzyl ester

HRID 1696835Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH:24]([N:26]2C(=O)C3C(=CC=CC=3)C2=O)[CH3:25])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C>[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH:24]([NH2:26])[CH3:25])=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution containing compound 25 (0.90 g, 1.81 mmol), hydrazine (0.26 mL, 5.42 mmol) and ethanol (10 mL) was heated at 75° C. for 3 h and then cooled to ambient temperature. The white precipitate was filtered under vacuum and washed with ethanol (3×5 mL). The filtrate and washings were combined and concentrated. The residue was subjected to column chromatography eluting with a mixture of methanol (0-15%), concentrated ammonium hydroxide (0-1.5%) and dichloromethane to afford the desired product 26 (0.59 g, 88%) as a white, waxy solid: 1H NMR (500 MHz, CD3OD) δ 1.08 (d, 3H), 1.36-1.80 (m, 8H), 2.55 (m, 4H), 2.88 (m, 1H), 3.10 (t, 2H), 5.08 (s, 2H), 7.08 (s, 4H), 7.34 (m, 5H); m/z (ESI) 369 [C23H32N2O2+H]+.

Workup

temperaturecooled to ambient temperature
filtrationThe white precipitate was filtered under vacuum
washwashed with ethanol (3×5 mL)
concentrationconcentrated
washeluting with a mixture of methanol (0-15%), concentrated ammonium hydroxide (0-1.5%) and dichloromethane

Sources & evidence

ORD record: ord-0e73ca1307874387adaf61b84fe8e84c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163758B2

Reaction notes

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