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

HRID 253509Notes

Reaction equation

HRID 253509 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)=[CH:10][C:9]=1[C:25]1[CH:34]=[CH:33][C:32]2[C:31]([CH3:36])([CH3:35])[CH2:30][CH2:29][C:28]([CH3:38])([CH3:37])[C:27]=2[CH:26]=1.[CH:39]1([NH2:42])[CH2:41][CH2:40]1>C(O)C>[CH:39]1([NH:42][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)=[CH:10][C:9]=2[C:25]2[CH:34]=[CH:33][C:32]3[C:31]([CH3:36])([CH3:35])[CH2:30][CH2:29][C:28]([CH3:38])([CH3:37])[C:27]=3[CH:26]=2)[CH2:41][CH2:40]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 66857022Ethyl 4'-(5-bromopentyloxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 11307422Ethyl 4'-(5-cyclopropylaminopentyloxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylateYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to that of Example 1b, by reaction of 600 mg (1 mmol) of ethyl 4′-(5-bromopentyloxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate with 720 μl (11.5 mmol) of cyclopropylamine in 50 ml of ethanol. 420 mg of ethyl 4′-(5-cyclopropylaminopentyloxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a white paste (yield=73%).

Sources & evidence

ORD record
ord-66f5b4df1efe48499d0618f65f20aa2c
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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