Allylamine → HCID 59132692, compound

HRID 1160315Notes

Reaction equation

HRID 1160315 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH2:13]([NH2:16])[CH:14]=[CH2:15].CCN(CC)CC>C1COCC1>[CH2:13]([NH:16][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH3:12])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 8471TriethylamineHCID 1025262-(4-Hydroxyphenyl)propionic acid

Product 1

HCID 59132692HCID 59132692, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N′-Carbonyldiimidazole (22.65 g, 140 mmol) was added to commercially available 2-(4-hydroxyphenyl)propionic acid (21 g, 127 mmol) in THF (100 mL). Gentle warming and gas evolution was observed. The resulting mixture was stirred for 3 h. Allylamine (10.9 g, 190.5 mmol) and Et3N (19.2 mL, 190.5 mmol) were added dropwise, and the mixture was stirred overnight. The reaction was quenched with water (200 mL) and the organic phase was extracted with ethyl acetate (50 mL×3). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The product was purified by flash chromatography (elution with ethyl acetate). Phenol 49.1 was obtained as a white solid. MS ESI m/e: 206 (M−H).

Workup

  1. temperatureGentle warming
  2. stirringthe mixture was stirred overnight
  3. customThe reaction was quenched with water (200 mL)
  4. extractionthe organic phase was extracted with ethyl acetate (50 mL×3)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (elution with ethyl acetate)

Sources & evidence

ORD record
ord-cac1f41036574eef8ccbbe7952af3dad
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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