Triethylamine → HCID 71612644, compound

HRID 516811Notes

Reaction equation

HRID 516811 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([OH:13])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH2:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[C:23]#[N:24])=[O:17].C(N(CC)CC)C>ClCCl>[OH:13][CH:4]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][NH:2][CH2:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[C:23]#[N:24])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27250723-Amino-1-Phenoxy-2-Propanol HydrochlorideHCID 154801851-(2-Chloroacetyl)pyrrolidine-2-carbonitrile

Product 1

HCID 71612644HCID 71612644, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-amino-3-phenoxypropan-2-ol hydrochloride (7.9 g, 38.8 mmol) and 1-(2-chloroacetyl)pyrrolidine-2-carbonitrile (6.1 g, 35.3 mmol) in DCM (250 mL) was added triethylamine (15 mL, 106 mmol). The mixture was stirred at room temperature overnight. After the TLC showed that the reaction was complete, the mixture was washed by brine. The aqueous solution was extracted with dichloromethane (DCM) (3×100 mL) and the combined DCM solution was concentrated to give a crude product, which was purified by column chromatography to give 3.5 g of 1-(2-(2-hydroxy-3-phenoxypropylamino)acetyl)pyrrolidine-2-carbonitrile (as shown at 6). Yield was 33.6%.

Workup

  1. washthe mixture was washed by brine
  2. extractionThe aqueous solution was extracted with dichloromethane (DCM) (3×100 mL)
  3. concentrationthe combined DCM solution was concentrated
  4. customto give a crude product, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-79e546d14e7e495aa4b9737f448d38e1
Source dataset
uspto-grants-2015_08
Patent number
US09115082B2

Reaction notes

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