Tert-Butylamine → HCID 20029889, compound

HRID 2050057Notes

Reaction equation

HRID 2050057 reaction equation
[O:1]1[CH2:17][CH:2]1[CH2:3][O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:8]([CH:15]=[O:16])=[CH:7][CH:6]=1.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>>[C:18]([NH:22][CH2:17][CH:2]([OH:1])[CH2:3][O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:8]([CH:15]=[O:16])=[CH:7][CH:6]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 20029918HCID 20029918, compound

Product 1

HCID 20029889HCID 20029889, compound

Conditions

Temperature
45 °C

Procedure

To 4-(2,3-epoxypropoxy)-5,6,7,8-tetrahydronapthaldehyde (2.4 gms) is added tert.-butylamine (15 ml.). The resulting solution is heated at 45° C. for 15 hours. The excess tert.-butylamine is removed at reduced pressure (20 mm). To the residue is added 30 ml. 6 N hydrochloride acid, and the resulting mixture is refluxed for three hours. The acidic mixture is poured into a saturated solution of sodium carbonate which is heated on a steam bath with nitrogen bubbling through it. The basic mixture is extracted with chloroform, which is dried over anhydrous sodium sulfate, filtered and concentrated to give 2.3 g of 4-(3-tert.butylamino-2-hydroxypropoxy)-5,6,7,8-tetrahydronapthaldehyde as an oil.

Workup

  1. customThe excess tert.-butylamine is removed at reduced pressure (20 mm)
  2. additionTo the residue is added 30 ml
  3. temperature6 N hydrochloride acid, and the resulting mixture is refluxed for three hours
  4. additionThe acidic mixture is poured into a saturated solution of sodium carbonate which
  5. temperatureis heated on a steam bath with nitrogen bubbling through it
  6. extractionThe basic mixture is extracted with chloroform, which
  7. dry with materialis dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0fac430c28ba4f609dee1d5c3c24a869
Source dataset
uspto-grants-1980_04
Patent number
US04199580

Reaction notes

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