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

HRID 1451147Notes

Reaction equation

HRID 1451147 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'-oxybis(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-218b64b96ac743e59c5e36472d0f0710
Source dataset
uspto-grants-1997_02
Patent number
US05604095

Reaction notes

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