Diethyl Ether → HCID 59693648, compound

HRID 1592836Notes

Reaction equation

HRID 1592836 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][O:20][CH:19]([C:23]#N)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O:27]CC)C>>[CH2:10]([N:17]1[CH2:22][CH2:21][O:20][CH:19]([C:23]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[O:27])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 156511954-Benzylmorpholine-2-carbonitrileHCID 178505773HCID 178505773, compound

Product 1

HCID 59693648HCID 59693648, compound

Procedure

A solution of 3-fluorophenylmagnesium bromide (0.5M, 50 ml, 25 mmol) was added dropwise to a stirred solution of 4-benzyl-mopholin-2-carbonitrile (4.59 g, 22.7 mmol) in diethyl ether (50 ml) at 0° C. under nitrogen. After 45 min at 0 C. the mixture was allowed to warm to room temperature for 30 min then recooled and quenched by the addition of aqueous hydrochloric acid (5M, 40 ml)—caution exothermic. After 30 min at room temperature, the acidic mixture was basified with sodium hydroxide (5M, 60 ml) and extracted with ethyl acetate (3×150 ml). The combined extracts were washed with brine solution, dried, filtered and concentrated in vacuo to give (+/−)-(4-benzyl-morpholin-2-yl)-(3-fluorophenyl)methanone (6.9 g) as a yellow oil.

Workup

  1. customquenched by the addition of aqueous hydrochloric acid (5M, 40 ml)—caution exothermic
  2. waitAfter 30 min at room temperature
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. washThe combined extracts were washed with brine solution
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2b83d43faa04c2ea954737cb4e5d3b6
Source dataset
uspto-grants-2007_11
Patent number
US07294623B2

Reaction notes

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