Dimethylcarbamoyl Chloride → HCID 55221038, compound

HRID 591707Notes

Reaction equation

HRID 591707 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18]>C1COCC1>[CH3:15][N:16]([CH3:20])[C:17]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:18]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 79341Piperidin-4-ol

Product 1

HCID 55221038HCID 55221038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxypiperidine (5.0 g, 49 mmol) in THF (70 mL) was added triethylamine (14.4 mL, 103 mmol) and dimethylcarbamyl chloride (9.0 mL, 98 mmol) slowly. The mixture was stirred at room temperature for 1.5 hours. The white precipitate was filtered off, washed with THF. The THF solution was concentrated to dryness then purified with column chromatography (SiO2, MeOH/CH2Cl2=1:19) to afford 4-hydroxypiperidine-1-carboxylic acid dimethylamide as colorless oil. Yield: 7.8 g (94%).

Workup

  1. filtrationThe white precipitate was filtered off
  2. washwashed with THF
  3. concentrationThe THF solution was concentrated to dryness
  4. customthen purified with column chromatography (SiO2, MeOH/CH2Cl2=1:19)

Sources & evidence

ORD record
ord-f8146b9b52824e8b8365b5fd23c32e94
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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