Cyclopentylamine → 1-(2-chloroethyl)-3-cyclopentylurea

HRID 2278954Notes

Reaction equation

HRID 2278954 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][CH2:8][CH2:9][N:10]=[C:11]=[O:12]>C1COCC1>[Cl:7][CH2:8][CH2:9][NH:10][C:11]([NH:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:12]

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 2555491-(2-chloroethyl)-3-cyclopentylureaYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of cyclopentylamine (4.63 mL, 47.0 mmol) in THF (235 mL) was treated drop-wise with 2-chloroethyl isocyanate (4.41 mL, 51.7 mmol) which was allowed to warm to RT, then concentrated to dryness. The solid was suspended in toluene and concentrated again to dryness to afford 1-(2-chloroethyl)-3-cyclopentylurea (8.95 g, 100%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.01 (d, J=7.3 Hz, 1 H), 5.91 (t, J=5.8 Hz, 1 H), 3.85-3.76 (m, 1 H), 3.54 (t, J=6.2 Hz, 2 H), 3.27 (q, J=6.1 Hz, 2 H), 1.78-1.69 (m, 2 H), 1.62-1.53 (m, 2 H), 1.51-1.42 (m, 2 H), 1.30-1.20 (m, 2 H); MS (ESI) m/z: 191.1 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. concentrationconcentrated again to dryness

Sources & evidence

ORD record
ord-79b4931e235b450292132353bdfdb866
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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