Borane → 3-Pyridinehexanamine

HRID 1583398Notes

Reaction equation

HRID 1583398 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH2:14])=O)[CH:2]=1.B>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:14])[CH:2]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 135575276-(Pyridin-3-YL)hexanamide

Product 1

HCID 135574533-PyridinehexanamineYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cold solution of 16.27 g of 3-pyridinehexanamide in 250 ml of dry tetrahydrofuran was added 300 ml of a 1M solution of borane in tetrahydrofuran. The mixture was heated to reflux over night, cooled, quenched with water, and made strongly acidic with 6N hydrochloric acid solution. The acidic solution was allowed to stand over night, made basic with sodium hydroxide solution, and was extracted with 3×150 ml of dichloromethane. The combined organic layers were dried over potassium carbonate, evaporated, and the residue was distilled to give 10.20 g (68%) of 3-pyridinehexanamine, bp 140°-150° C./0.2 mm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux over night
  3. temperaturecooled
  4. customquenched with water
  5. waitto stand over night
  6. extractionwas extracted with 3×150 ml of dichloromethane
  7. dry with materialThe combined organic layers were dried over potassium carbonate
  8. customevaporated
  9. distillationthe residue was distilled

Sources & evidence

ORD record
ord-6bac5f17b6d247f48cf0c37d4667f55d
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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