2-Bromoethylamine hydrobromide → 1,8-Diamino-3-oxa-6-azaoctane

HRID 863734Notes

Reaction equation

HRID 863734 reaction equation
Cl.Cl.[O:3]([CH2:7][CH2:8][NH2:9])[CH2:4][CH2:5][NH2:6].Br.Br[CH2:12][CH2:13][NH2:14].C[O-].[Na+]>C(O)C>[NH2:6][CH2:5][CH2:4][O:3][CH2:7][CH2:8][NH:9][CH2:12][CH2:13][NH2:14]

Participants

5

Reactant 3

HCID 27742172-Bromoethylamine hydrobromideHCID 28290232,2'-Oxybis(ethylamine) hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 199738321,8-Diamino-3-oxa-6-azaoctane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2,2'-oxy-bis(ethylamine)dihydrochloride (1) (177 mg, 1 mmol), bromoethylamine hydrobromide (2) (204.9 mg, 1 mmol), in ethanol (10 mL) was added sodium methoxide (162.6 mg, 3 mmol) at room temperature. The reaction mixture was refluxed for 48 hours under a positive flow of argon. Reaction mixture was cooled to room temperature, ethanol was evaporated on rotavapor and the crude product (135 mg) was directly taken into next step to prepare the bis-naphthalimide, compound 5.

Workup

  1. temperatureThe reaction mixture was refluxed for 48 hours under a positive flow of argon
  2. customReaction mixture
  3. customethanol was evaporated on rotavapor
  4. customto prepare the bis-naphthalimide, compound 5

Sources & evidence

ORD record
ord-b8bac8ae5b584f38b78e6952feed6e86
Source dataset
uspto-grants-1996_10
Patent number
US05561042

Reaction notes

Loading…