Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276616Notes

Reaction equation

HRID 276616 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1.I[C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[S:21])=[C:15](C(C)C)[CH:14]=1.[OH:25]CCN.O=S(Cl)Cl>>[OH:25][CH2:4][C:5]1([NH2:6])[CH2:3][CH2:2][CH2:8][CH2:7]1.[I:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:20]2[S:21][CH2:15][C:16]3([CH2:14][CH2:13][CH2:18][CH2:17]3)[NH:19]2)=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 24386Thionyl ChlorideHCID 126679384-Iodo-2-(propan-2-yl)anilineHCID 183165064-Iodo-2-isopropylphenyl isothiocyanate2×

Product 2

HCID 663071-AminocyclopentanemethanolHCID 178439352HCID 178439352, compound

Procedure

4-Iodo-2-isopropylaniline was converted to 4-iodo-2-isopropylphenyl isothiocyanate according to Method A2b. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was sequentially reacted with SOCl2 and 4-iodo-2-isopropylphenyl isothiocyanate according to Method C2a to give 2-(4-iodo-2-isopropylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(4-iodo-2-isopropylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane. The phenyl iodide was reacted with CuCN according to Method D7a to afford 2-(4-cyano-2-isopropylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-e7fd45ebbf7d426ba8c5e5f6e2cdeb76
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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