Water → [8-(3-Methoxypropyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine

HRID 1948612Notes

Reaction equation

HRID 1948612 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1([C:13]#N)[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1.[NH4+].[Cl-].O.C1[CH2:23][O:22][CH2:21][CH2:20]1>>[CH3:23][O:22][CH2:21][CH2:20][CH2:13][C:3]1([N:2]([CH3:15])[CH3:1])[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 68842849[8-(3-Methoxypropyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine

Procedure

A solution of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (9.68 g, 46 mmole) in absolute THF (30 ml) was added dropwise while cooling with ice. A viscous precipitate thereby formed, and 100 ml of absolute THF was therefore added to achieve a better mixing. The mixture was stirred for 24 hours at room temperature. 20% NH4Cl solution (100 ml) and water (120 ml) were added while cooling with ice to the reaction mixture, and the organic phase was separated and the aqueous phase was extracted with ether (3×120 ml).

Workup

  1. temperaturewhile cooling with ice
  2. customA viscous precipitate thereby formed
  3. additiona better mixing
  4. temperaturewhile cooling with ice to the reaction mixture
  5. customthe organic phase was separated
  6. extractionthe aqueous phase was extracted with ether (3×120 ml)

Sources & evidence

ORD record
ord-bf8696cb4115401ea40a91df6aa4f6b2
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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