1-[3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-pyrrolidinecarbonitrile → 1-(3-Aminopropyl)-3-pyrrolidinecarbonitrile

HRID 1669214Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH:17]([C:20]#[N:21])[CH2:16]1>CCO>[NH2:3][CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH:17]([C:20]#[N:21])[CH2:16]1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of phthalimide 303 (5.96 g, 21.0 mmol) and N2H4.H2O (2.04 mL, 42.0 mmol in EtOH (60 mL) was stirred at reflux temperature for 2 h. The solution was cooled to 5° C. for 2 h, the precipitate filtered, washed with EtOH (5 mL) and the filtrate evaporated to half volume. The solution was cooled at 5° C. for a further 2 h, the precipitate filtered, washed with EtOH (5 mL) and the filtrate evaporated to give diamine 304 which was used without further purification: 1H NMR δ 2.94-3.02 (m, 1H, CHCN), 2.90 (dd, J=9.0, 7.9 Hz, 1H, CH2), 2.82 (t, J=6.8 Hz, 2H, CH2N), 2.61-2.68 (m, 2H, CH2N), 2.48-2.58 (m, 3H, CH2N), 2.05-2.15 (m, 1H, CH2), 2.03-2.11 (m, 1H, CH2), 1.68 (p, J=7.0 Hz, 2H, CH2), NH2 not observed.

Workup

temperatureat reflux temperature for 2 h
filtrationthe precipitate filtered
washwashed with EtOH (5 mL)
customthe filtrate evaporated to half volume
temperatureThe solution was cooled at 5° C. for a further 2 h
filtrationthe precipitate filtered
washwashed with EtOH (5 mL)
customthe filtrate evaporated

Sources & evidence

ORD record: ord-55088f1bdcd643038721cd76ce15dcd7
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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