Water → 4-(Piperidin-1-yl)butan-1-ol

HRID 2274402Notes

Reaction equation

HRID 2274402 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.Cl.[N:13]1([CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>CCOCC>[N:13]1([CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 131720814-(Piperidin-1-yl)butanoic acid hydrochlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 4189434-(Piperidin-1-yl)butan-1-olYield 85.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

11.68 mL of a 1M solution of lithium aluminum hydride in ether are added to 10 mL of tetrahydrofuran, and then 1 g of 4-piperidin-1-ylbutyric acid hydrochloride (synthesized according to a method described in the literature) is added. The medium is brought to boiling for approximately 10 minutes. After a return to ambient temperature and cooling to 0° C., a mixture of 1 mL of distilled water-30 mL of tetrahydrofuran is added dropwise. A large amount of gas is given off and strong exothermia is observed. After a return to ambient temperature, the medium is evaporated to dryness under reduced pressure in a rotary evaporator. The reaction crude is triturated in 150 mL of ethyl acetate and filtered, and the filtrate is washed with 2×20 mL of distilled water. The organic phase is dried over magnesium sulfate, filtered and then concentrated under vacuum in a rotary evaporator. 646 mg of 4-piperidin-1-ylbutan-1-ol are isolated in the form of a colorless oil. 1H NMR (300 MHz, DMSO-d6, δ in ppm): from 1.30 to 1.53 (m, 10H); 2.20 (t, J=6.5 Hz, 2H); 2.28 (m, 4H); 3.37 (broad t, J=6.5 Hz, 2H); 4.57 (broad s, 1H).

Workup

  1. additionis added
  2. additionis added dropwise
  3. customAfter a return to ambient temperature, the medium is evaporated to dryness under reduced pressure in a rotary evaporator
  4. customThe reaction crude
  5. customis triturated in 150 mL of ethyl acetate
  6. filtrationfiltered
  7. washthe filtrate is washed with 2×20 mL of distilled water
  8. dry with materialThe organic phase is dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum in a rotary evaporator

Sources & evidence

ORD record
ord-80c5de2545024558a9b715ac14f40dc9
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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