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

HRID 253496Notes

Reaction equation

HRID 253496 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=2)=[CH:9][C:8]=1[C:24]1[CH:33]=[CH:32][C:31]2[C:30]([CH3:35])([CH3:34])[CH2:29][CH2:28][C:27]([CH3:37])([CH3:36])[C:26]=2[CH:25]=1.[CH:38]1([NH2:41])[CH2:40][CH2:39]1>C(O)C>[CH:38]1([NH:41][CH:4]([CH2:3][CH3:2])[CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=3)=[CH:9][C:8]=2[C:24]2[CH:33]=[CH:32][C:31]3[C:30]([CH3:35])([CH3:34])[CH2:29][CH2:28][C:27]([CH3:37])([CH3:36])[C:26]=3[CH:25]=2)[CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 66856889Ethyl 4'-(4-chlorobutoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 66856286Ethyl 4'-(2-cyclopropylaminobutoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylateYield 25.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to that of Example 1c, by reaction of 700 mg (1.3 mmol) of ethyl 4′-(4-chlorobutoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate with 800 μl (11.5 mmol) of cyclopropylamine in 100 ml of ethanol. 180 mg of ethyl 4′-(2-cyclopropylaminobutoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a yellow oil (yield=26%).

Sources & evidence

ORD record
ord-dd8be8b7a55744f0bab5445712b9bbf6
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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