7-Tridecanone → Tridecan-7-amine

HRID 551753Notes

Reaction equation

HRID 551753 reaction equation
[CH2:1]([C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>CO>[CH2:1]([CH:7]([NH2:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 100157-TridecanoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 574991Tridecan-7-amineYield 116.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 mL round bottom flask, 5.00 g (25.5 mmol) dihexylketone, 19.7 g (255 mmol) ammonium acetate, and 1.10 g (17.8 mmol) sodium cyanoborohydride (NaBH3CN) were dissolved in 75 mL absolute MeOH and stirred at room temperature for 48 hours, until no significant amount of the starting material could be detected by NMR. The mixture was quenched by adding concentrated hydrochloric acid (HCl) dropwise (˜3 mL), then concentrated in vacuo. The resulting white solid was taken up in 500 mL water, basified to pH 10 with solid potassium hydroxide (KOH), and extracted with chloroform (CHCl3) twice (200 mL each). The CHCl3 fractions were combined and concentrated to give 4.12 g (81%) of 1-hexylheptylamine 1 as a pale yellow oil. 1H NMR (D2O, 500 MHz): δ 0.73 (t, 6H), 1.15-1.23 (m, 16H), 1.55 (m, 4H), 3.13 (m, 1H).

Workup

  1. customThe mixture was quenched
  2. additionby adding concentrated hydrochloric acid (HCl) dropwise (˜3 mL)
  3. concentrationconcentrated in vacuo
  4. extractionextracted with chloroform (CHCl3) twice (200 mL each)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e5cf9284ca1c4c96bef0ce33f5efeb1d
Source dataset
uspto-grants-2011_05
Patent number
US07947837B2

Reaction notes

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