Hydrochloric Acid → 8-(1-Pyrrolidinyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

HRID 2244500Notes

Reaction equation

HRID 2244500 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[O:7]1[C:11]2([CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.[C-:18]#[N:19].[K+]>CO.O>[N:2]1([C:14]2([C:18]#[N:19])[CH2:15][CH2:16][C:11]3([O:10][CH2:9][CH2:8][O:7]3)[CH2:12][CH2:13]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 31268PyrrolidineHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 3609768-(1-Pyrrolidinyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 55 ml water, 33 ml hydrochloric acid (32 per cent by weight), 50 ml methanol, 127 ml pyrrolidine, 50.0 g 1,4-dioxaspiro[4.5]decan-8-one and 50.0 g potassium cyanide was stirred for 65 hours at room temperature. The pale brown suspension obtained was extracted four times with 50 ml diethyl ether each time, the combined extracts were dried over sodium sulfate, filtered and concentrated and the residue was largely freed from solvent residues in vacuo. 76.7 g 8-pyrrolidin-1-yl-1,4-dioxaspiro[4.5]decane-8-carbonitrile were obtained as a pale brown liquid.

Workup

  1. customThe pale brown suspension obtained
  2. extractionwas extracted four times with 50 ml diethyl ether each time
  3. dry with materialthe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ba42583d624423786341a7988afa682
Source dataset
uspto-grants-2010_03
Patent number
US07678834B2

Reaction notes

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