Dimethylamine → Benzyl 5-(dimethylamino)pentanoate

HRID 537823Notes

Reaction equation

HRID 537823 reaction equation
CS([CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])(=O)=O.[CH3:19][NH:20][CH3:21]>C(O)C>[CH3:19][N:20]([CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 57500205HCID 57500205, compound

Product 1

HCID 66632292Benzyl 5-(dimethylamino)pentanoateYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl 5-(methanesulfonyl)pentanoate (1.39 g, 4.85 mmol) was allowed to react in a 5.6M solution of dimethylamine in ethanol (100 mL) for 20 hours. The solution was then concentrated in vacuo to dryness. The resulting brown oil was purified by column chromatography (column 10″L×1″W; eluted with a gradient of 100% dichloromethane→2%/0.5%→4%/0.5% MeOH/NH4OH in dichloromethane) to afford the product as a yellow oil (0.79 g, 69%).

Workup

  1. concentrationThe solution was then concentrated in vacuo to dryness
  2. customThe resulting brown oil was purified by column chromatography (column 10″L×
  3. washeluted with a gradient of 100% dichloromethane→2%/0.5%→4%/0.5% MeOH/NH4OH in dichloromethane)

Sources & evidence

ORD record
ord-816f57507e0a4f109b4e4610b7c43cfd
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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