(+-)-1-Aminoindan → 6-Bromo-2,3-dihydro-1H-inden-1-amine

HRID 1818012Notes

Reaction equation

HRID 1818012 reaction equation
[CH:1]1([NH2:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Br:11]C1C=C2C(CCC2=O)=CC=1.[BH3-]C#N.[Na+]>>[Br:11][C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][CH:1]2[NH2:10])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 123445(+-)-1-AminoindanHCID 1397781-Indanone, 6-bromo-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 162443156-Bromo-2,3-dihydro-1H-inden-1-amine

Procedure

The title indanamine was generated from 6-bromo-1-indanone (2.00 g, 9.50 mmol), NaBH3CN (4.20 g, 66.84 mmol) and NH4OAc (22.00 g, 0.29 mol) according to the protocols as outlined in general procedure C. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 1.59-1.73 (m, 3H), 2.44-2.56 (m, 1H), 2.70-2.82 (m, 1H), 2.84-2.98 (m, 1H), 4.29-4.40 (m, 1H), 6.98-7.18 (m, 1H), 7.26-7.38 (m, 1H), 7.4 (s, 1H).

Sources & evidence

ORD record
ord-a2d6d335a1a34e219bcdce2db16a5ee3
Source dataset
uspto-grants-2009_10
Patent number
US07598417B2

Reaction notes

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