3,4-Dichlorophenethylamine → N-[2-(3,4-dichlorophenyl)ethyl]-2',3'-dihydro-spiro [cyclopropane-1,1'-[1H]indene]-5'-methanamine

HRID 855314Notes

Reaction equation

HRID 855314 reaction equation
C1(C2C=CC(CNCCC3C=CC(F)=C(C(F)(F)F)C=3)=CC=2)CC1.[C:25]12([CH2:37][CH2:36]1)[C:33]1[C:28](=[CH:29][C:30]([CH:34]=O)=[CH:31][CH:32]=1)[CH2:27][CH2:26]2.[Cl:38][C:39]1[CH:40]=[C:41]([CH2:46][CH2:47][NH2:48])[CH:42]=[CH:43][C:44]=1[Cl:45].[BH4-].[Na+]>>[Cl:38][C:39]1[CH:40]=[C:41]([CH2:46][CH2:47][NH:48][CH2:34][C:30]2[CH:29]=[C:28]3[C:33](=[CH:32][CH:31]=2)[C:25]2([CH2:37][CH2:36]2)[CH2:26][CH2:27]3)[CH:42]=[CH:43][C:44]=1[Cl:45]

Participants

5

Reactant 4

HCID 2179583,4-DichlorophenethylamineHCID 4311764Sodium borohydrideHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amineHCID 860938352',3'-Dihydrospiro[cyclopropane-1,1'-indene]-5'-carbaldehyde

Product 1

HCID 69513426N-[2-(3,4-dichlorophenyl)ethyl]-2',3'-dihydro-spiro [cyclopropane-1,1'-[1H]indene]-5'-methanamineYield 92.2%

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 (62 mg, 0.36 mmol), 2-(3,4-dichloro-phenyl)-ethylamine (68 mg, 0.36 mmol) and sodium borohydride (20 mg, 0.54 mmol). The desired product (115 mg, 92%) was isolated without further purification as a colorless oil. MS (ISP) 346.2 (M+H)+.

Sources & evidence

ORD record
ord-54b0e3723efb486b9c60847302e496dc
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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