Hydrochloric Acid → N-heptyl-4-butylbenzenemethanamine

HRID 359996Notes

Reaction equation

HRID 359996 reaction equation
[CH2:1]([NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl>O1CCCC1>[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13733121Benzamide, 4-butyl-N-heptyl-

Product 1

HCID 15137718N-heptyl-4-butylbenzenemethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 38.0 g of N-heptyl-4-n-butylbenzamide and 280 ml of borane-tetrahydrofuran complex in 120 ml of anhydrous tetrahydrofuran was refluxed for 18 hours, allowed to cool, and treated with 6N hydrochloric acid. The organic solvent was evaporated and the residue was partitioned between ether and aqueous sodium hydroxide solution. The ether layer was separated, dried, and evaporated. The residue was distilled to yield N-heptyl-4-n-butylbenzenemethanamine as a colorless liquid, bp 115°C. at 80μ.

Workup

  1. temperatureto cool
  2. customThe organic solvent was evaporated
  3. customthe residue was partitioned between ether and aqueous sodium hydroxide solution
  4. customThe ether layer was separated
  5. customdried
  6. customevaporated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-931275d5ae124c35b72b6a8335895b6e
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

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