Butylamine → Ethyl 4'-(3-butylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

HRID 253489Notes

Reaction equation

HRID 253489 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].I[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[CH:13][C:12]=1[C:28]1[CH:37]=[CH:36][C:35]2[C:34]([CH3:39])([CH3:38])[CH2:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]=2[CH:29]=1>C(O)C>[CH2:1]([NH:5][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:22]=2)=[CH:13][C:12]=1[C:28]1[CH:37]=[CH:36][C:35]2[C:34]([CH3:39])([CH3:38])[CH2:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]=2[CH:29]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 66856963Ethyl 4'-(3-iodopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 11330179Ethyl 4'-(3-butylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylateYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to that of Example 1c, by reaction of 1.9 ml (19.3 mmol) of n-butylamine and 750 mg (1.29 mmol) of ethyl 4′-(3-iodopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate (obtained in Example 1b) in 50 ml of ethanol. 380 mg of ethyl 4′-(3-butylaminopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a white solid (m.p.=175° C., yield=59%).

Sources & evidence

ORD record
ord-3ca22eb1f005499aae3b539f4b087a3c
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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