Hydrochloric Acid → HCID 178479215, compound

HRID 487884Notes

Reaction equation

HRID 487884 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10])#[N:2].CO.[ClH:13].[CH:14]1([CH2:17][NH2:18])[CH2:16][CH2:15]1>C(Cl)Cl>[ClH:13].[CH2:15]1[CH2:16][CH:14]1[CH2:17][NH:18][C:1]([CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10])=[NH:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 75646CyclopropanemethanamineHCID 1245083165195-19-9

Product 1

HCID 178479215HCID 178479215, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of N-(cyanoethyl)oxazolidinone 18 (30 g, 0.21 mol) in dry methanol (10.9 g, 0.34 mol) and dry CH2Cl2 (60 mL) was saturated with dry HCl at -15° to 0° C. The mixture was then stirred for 6 h at 0°-20° C. The mixture was evaporated and dried in vacuo for 1 h. The crystalline imidoester hydrochloride was dissolved in dry methanol (120 mL) and cooled to -15° C. To the stirred solution cyclopropylmethylamine (31.2 g, 0.44 mol) was added in drops over a period of 20 min while maintaining the temperature at -15 to 0° C. The mixture was then stirred at -10° C. for 45 min and evaporated. The residue was dissolved in methanol, treated with ether until turbid and was refrigerated for 6 days. The colorless crystalline material was collected and dried to give 59 (28.7 g, 55%), mp 86°-88° C. 1H NMR (DMSO--d6) δ 0.28 (m, 2, --CH--CH2), 0.55 (m, 2, --CH--CH2), 1.05 (m, 1, --CH), 2.68 [t, 2, --CH2 --C(N=)], 3.07 (d, 2, --NH--CH2), 3.54 [t, 2, --CH2 --CH2 --C(N=)], 3.67 (t, 2, --O--CH2 --CH2). 4.30 (t, 2, --OCH2).

Workup

  1. customThe mixture was evaporated
  2. customdried in vacuo for 1 h
  3. dissolutionThe crystalline imidoester hydrochloride was dissolved in dry methanol (120 mL)
  4. temperaturewhile maintaining the temperature at -15 to 0° C
  5. stirringThe mixture was then stirred at -10° C. for 45 min
  6. customevaporated
  7. dissolutionThe residue was dissolved in methanol
  8. additiontreated with ether until turbid
  9. waitwas refrigerated for 6 days
  10. customThe colorless crystalline material was collected
  11. customdried

Sources & evidence

ORD record
ord-8f4ffc862396413eba4d42d5c9dfed7a
Source dataset
uspto-grants-1994_03
Patent number
US05298499

Reaction notes

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