Cyclopropylamine → HCID 62603281, compound

Using an addition funnel, a solution of 5-bromopentene (15.75 g, 106 mmol) in 50 mL of methanol was added over the course of 5 min to a solution of cyclopropylamine (20.6 g, 361 mmol) in 200 mL of methanol. This solution was allowed to stir at rt for 72 h at which time is was refluxed for 1 h. The methanol and excess cyclopropylamine were removed by distillation. The residue, hydrobromide salt of the product, was partitioned between ether and 4 N NaOH. The aqueous phase was washed with ether (2×). The combined ether extracts were dried (MgSO4), filtered, and concentrated to give 8 g (60%) of N-(pent-4-enyl)cyclopropanamine as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 0.31-0.36 (m, 2H) 0.40-0.46 (m, 2H) 1.53-1.63 (m, 2H) 1.87 (brs, 1H) 2.05-2.10 (m, 2H) 2.10-2.14 (m, 1H) 2.69 (t, J=7.32 Hz, 2H) 4.91-5.07 (m, 2H) 5.72-5.88 (m, 1H).

1. temperatureis was refluxed for 1 h
2. customThe methanol and excess cyclopropylamine were removed by distillation
3. customThe residue, hydrobromide salt of the product, was partitioned between ether and 4 N NaOH
4. washThe aqueous phase was washed with ether (2×)
5. dry with materialThe combined ether extracts were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-95b43d7d11cf4796a2696accf2a4a829

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003604B2