P-Anisidine → HCID 532253, compound

HRID 1700046Notes

Reaction equation

HRID 1700046 reaction equation
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(C(F)(F)C(F)C(F)(F)F)CC)C.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1>C(OCC)C>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:11]([C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)=[O:13])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 132351-Adamantanecarboxylic acidHCID 136149N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine

Product 1

HCID 532253HCID 532253, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Adamantanecarboxylic acid (10.8 g, 0.06 mole) was dissolved in N,N-diethyl-1,1,2,3,3,3-hexafluoropropylamine (13.4 g, 0.06 mole) as described in example 1. After the reaction mixture cooled to room temperature, a solution of p-anisidine (18.5 g, 0. 15 mole) in ethyl ether (minimum amount) was added and the reaction mixture was stirred for about an hour. The ethyl ether was removed at the rotary evaporator and the N-p-methoxyphenyl-1-adamantanecarboxamide was isolated as described in example 1 to give 15.8 g, 92%; mp 186-187° C. The analytical sample was recrystallized from cyclohexane and sublimed. Anal. Calcd. for C18H23NO2: C, 75.80; H, 8.07; N, 4.91. Found: C, 75.69; H, 8.17; N, 4.92.

Workup

  1. customThe ethyl ether was removed at the rotary evaporator

Sources & evidence

ORD record
ord-33922ef9e1c84d0b850c7b00c4c5823e
Source dataset
uspto-grants-2002_02
Patent number
US06348625B1

Reaction notes

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