Phenethylamine, m-trifluoromethyl- → 2',3'-dihydro-N-[2-[3-(trifluoromethyl)phenyl]ethyl]-spiro[cyclopropane-1,1'-[1H]indene]-5'-methanamine

HRID 855315Notes

Reaction equation

HRID 855315 reaction equation
[CH:1]1([C:4]2[CH:24]=[CH:23][C:7]([CH2:8][NH:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15](F)=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[C:25]12(CC1)C1C(=CC(C=O)=CC=1)C[CH2:26]2.FC(F)(F)C1C=C(CCN)C=CC=1.[BH4-].[Na+]>>[F:21][C:19]([F:22])([F:20])[C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][NH:9][CH2:8][C:7]2[CH:6]=[C:5]3[C:4](=[CH:24][CH:23]=2)[C:1]2([CH2:2][CH2:3]2)[CH2:26][CH2:25]3)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 104223Phenethylamine, m-trifluoromethyl-HCID 4311764Sodium borohydrideHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amineHCID 860938352',3'-Dihydrospiro[cyclopropane-1,1'-indene]-5'-carbaldehyde

Product 1

HCID 695134182',3'-dihydro-N-[2-[3-(trifluoromethyl)phenyl]ethyl]-spiro[cyclopropane-1,1'-[1H]indene]-5'-methanamineYield 88%

Procedure

The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 2′,3′-dihydro-spiro-[cyclopropane-1,1′-[1H]indene]-5′-carboxaldehyde (prepared as described in example S108) (68 mg, 0.40 mmol), 2-(3-trifluoromethylphenyl)-ethylamine (75 mg, 0.40 mmol) and sodium borohydride (22 mg, 0.59 mmol). The desired product (120 mg, 88%) was isolated without further purification as a colorless oil. MS (ISP) 346.3 (M+H)+.

Sources & evidence

ORD record
ord-dc85c6bbee3e44b9a7fedf59e2af67f3
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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