Hydrochloric Acid → 4-(Pyrrolidin-1-ylmethyl)piperidine

HRID 1179347Notes

Reaction equation

HRID 1179347 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[N:15]1([CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 589780244-Pyrrolidin-1-ylmethyl-piperidine-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 167683474-(Pyrrolidin-1-ylmethyl)piperidineYield 53.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of the product of Example 3 (2.4 g) in dioxane (30 mL) was added 4 N HCl in dioxane (30 mL). The resulting mixture was stirred at room temperature overnight, concentrated, and treated with 10% NaOH (50 mL). The resulting mixture was extracted with DCM (2×100 mL). The combined extracts were washed with water (30 mL) and brine (30 mL), and concentrated under reduced pressure to give the title compound as a brown-yellow oil (0.81 g).

Workup

  1. concentrationconcentrated
  2. additiontreated with 10% NaOH (50 mL)
  3. extractionThe resulting mixture was extracted with DCM (2×100 mL)
  4. washThe combined extracts were washed with water (30 mL) and brine (30 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-440349db05ba405689ed7d91bf16bc45
Source dataset
uspto-grants-2007_10
Patent number
US07279491B2

Reaction notes

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