Dimethylcarbamoyl Chloride → HCID 68003686, compound

HRID 1896931Notes

Reaction equation

HRID 1896931 reaction equation
Cl.[O:2]1[C:6]2([CH2:11][CH2:10][CH:9]([CH:12]([NH2:15])[CH2:13][CH3:14])[CH2:8][CH2:7]2)[O:5][CH2:4][CH2:3]1.[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19]>ClCCl>[O:2]1[C:6]2([CH2:11][CH2:10][CH:9]([CH:12]([NH:15][C:18]([N:17]([CH3:21])[CH3:16])=[O:19])[CH2:13][CH3:14])[CH2:8][CH2:7]2)[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 680037861-1,4-Dioxaspiro[4.5]decan-8-ylpropan-1-amine hydrochloride

Product 1

HCID 68003686HCID 68003686, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 50 mL round-bottom flask was placed a solution of 1-1,4-dioxaspiro[4.5]decan-8-ylpropan-1-amine hydrochloride (as prepared in Example 104 Step B) (50 mg, 0.21 mmol, 1.00 equiv) in dichloromethane (10 mL) and TEA (42.8 mg, 0.42 mmol, 2.00 equiv). This was followed by the addition of dimethylcarbamic chloride (27.5 mg, 0.25 mmol, 1.20 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with 2×20 mL of dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The title compound was obtained as a yellow oil.

Workup

  1. customInto a 50 mL round-bottom flask was placed
  2. stirringThe resulting solution was stirred overnight at room temperature
  3. customThe reaction was then quenched by the addition of 20 mL of water
  4. extractionThe resulting solution was extracted with 2×20 mL of dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c6e1d4cb7a4f4eeda450645c4925a7f2
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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