Tert-Butylamine → HCID 21520272, compound

HRID 1282832Notes

Reaction equation

HRID 1282832 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C(OC(C1C2O[C:18]([C:21](=[O:24])[CH2:22]Br)=CC=2C=CC=1)C)(=O)C>C(OCC)C>[C:1]([NH:5][CH2:18][C:21]([CH2:22][NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:24])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 21520277HCID 21520277, compound

Product 1

HCID 21520272HCID 21520272, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.9 g of tertbutylamine was added dropwise at 10°C at a stirred solution of 0.975 g of 7-(1'-acetoxyethyl)-2-bromoacetylbenzofuran (prepared as described in the penultimate paragraph of part A of Example 1) in 20 ml of dry diethyl ether. The mixture was then allowed to stand at 0°C for 20 hours. The cold solution was filtered and the filtrate extracted with dilute hydrochloric acid. The acidic extract was made basic with dilute aqueous sodium hydroxide solution and extracted twice with diethyl ether. The combined extracts were washed with water and with brine and then dried over anhydrous sodium sulphate. The sodium sulphate was filtered off, the filtrate evaporated to dryness under reduced pressure and the crude, unstable 7-(1'-acetoxyethyl)-2-benzofuranyl, (tertbutylaminomethyl) ketone obtained was used in the process without further purification.

Workup

  1. customprepared
  2. filtrationThe cold solution was filtered
  3. extractionthe filtrate extracted with dilute hydrochloric acid
  4. extractionThe acidic extract
  5. extractionextracted twice with diethyl ether
  6. washThe combined extracts were washed with water and with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationThe sodium sulphate was filtered off
  9. customthe filtrate evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-70a90b00db004703a04f8c90049f3aef
Source dataset
uspto-grants-1976_08
Patent number
US03972900

Reaction notes

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