Piperidine, 1-(2-chloroethyl)-, hydrochloride → 3-{4-methoxy-3-[5,5,8,8-tetramethyl-3-(2-piperidin-1-yl-ethoxy)-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic Acid

HRID 988043Notes

Reaction equation

HRID 988043 reaction equation
[OH:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][C:26]([O:28]CC)=[O:27])[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.Cl.Cl[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH3:23][O:22][C:21]1[CH:20]=[CH:19][C:18]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])=[CH:17][C:16]=1[C:3]1[C:2]([O:1][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[CH:11][C:10]2[C:9]([CH3:13])([CH3:12])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 69792380Ethyl 3-[3-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl)acrylate

Product 1

HCID 697927113-{4-methoxy-3-[5,5,8,8-tetramethyl-3-(2-piperidin-1-yl-ethoxy)-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic AcidYield 93.9%

Procedure

In a manner similar to that of Example 16(a), by reaction of 1.4 g (3.4 mmol) of ethyl 3-[3-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]acrylate obtained in Example 13(f) and 760 mg (4.08 mmol) of 1-(2-chloroethyl)piperidine hydrochloride, 1.57 g (89%) of the expected compound was obtained in the form of a colorless oil.

Sources & evidence

ORD record
ord-3a8e39ed89444d46b7e5feac4f20ec5e
Source dataset
uspto-grants-2003_10
Patent number
US06632963B1

Reaction notes

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