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

HRID 253487Notes

Reaction equation

HRID 253487 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.I[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)=[CH:12][C:11]=1[C:27]1[CH:36]=[CH:35][C:34]2[C:33]([CH3:38])([CH3:37])[CH2:32][CH2:31][C:30]([CH3:40])([CH3:39])[C:29]=2[CH:28]=1>C(O)C>[CH:1]1([NH:4][CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=3)=[CH:12][C:11]=2[C:27]2[CH:36]=[CH:35][C:34]3[C:33]([CH3:38])([CH3:37])[CH2:32][CH2:31][C:30]([CH3:40])([CH3:39])[C:29]=3[CH:28]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 66856963Ethyl 4'-(3-iodopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 11398367Ethyl 4'-(3-cyclopropylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylateYield 59.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to that of Example 1c, by reaction of 1.7 ml (24.5 mmol) of cyclopropylamine with 670 mg (1.12 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. 350 mg of ethyl 4′-(3-cyclopropylaminopropoxy)-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.=141° C., yield=59%).

Sources & evidence

ORD record
ord-9ad32edfea944c87b810877cc518aee6
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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