Tert-Butylamine → HCID 20029889, compound

HRID 235928Notes

Reaction equation

HRID 235928 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. 6N hydrochloric 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. temperature6N hydrochloric 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-13958f1a3c5d41b2914831ef114fb08c
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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