Phenol → HCID 18621550, compound

HRID 324550Notes

Reaction equation

[C:1]([N:4]1[CH2:18][CH2:17][CH:7]([C:8]([O:10]C2C=CC=CC=2)=O)[CH2:6][CH2:5]1)(=O)[CH3:2].[C:19](N1CCC(C(Cl)=O)CC1)(=[O:21])C.[C:31]1([OH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CCN(CC)CC>C1COCC1.CCOC(C)=O>[OH:37][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:8]([CH:7]1[CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH2:19][OH:21])[CH2:18][CH2:17]1)=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

Phenyl N-acetylisonipecotate. To a suspension of N-acetylisonipecotoyl chloride (3.70 g, 19.50 mmol) in THF (60 mL) were added phenol (2.70 g, 27 mmol) and Et3N (5.0 mL, 36 mmol). The resulting heterogeneous mixture was stirred at 25° C. for 20 h, diluted with EtOAc (50 mL) and was washed with a saturated solution of NH4Cl (50 mL). The crude compound was purified by filtration on silica gel using EtOAc/n-hexane as eluant to afford the title compound as a colorless solid (3.45 g, 80%): mp 96-98 C; 1H NMR (CDCl3) d 1.60-1.95 (m, 2H), 2.00-2.2 (m, 5H), 2.70-3.00 (m, 2H), 3.10-3.30 (m, 1H), 3.75-3.90 (m, 1H), 4.40-4.60 (m, 1H), 7.06 (d, J=7.5 Hz, 2H), 7.22 (d, J=7.5 Hz, 1H), 7.38 (t, J=7.5 Hz, 2H).

Workup

washwas washed with a saturated solution of NH4Cl (50 mL)
filtrationThe crude compound was purified by filtration on silica gel

Sources & evidence

ORD record: ord-149df84270b84f6dafd48acba05854e9
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218404B1

Reaction notes

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