Potassium Iodide → Tert-butyl 4-cyano-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]piperidine-1-carboxylate

HRID 273023Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:20][CH2:21][N:22]([CH2:30][CH2:31]Cl)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].[H-].[Na+].[I-].[K+]>>[C:17]([C:16]1([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:15][CH:14]=2)[CH2:31][CH2:30][N:22]([C:23]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:29])[CH2:21][CH2:20]1)#[N:18]

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 24758Sodium hydride

HCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

HCID 23091635[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]acetonitrile

Product 1

HCID 68578770Tert-butyl 4-cyano-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]piperidine-1-carboxylateYield 53%

Procedure

The title compound (1.8 g, 53%) was prepared using [4-(3-pyrrolidin-1-ylpropoxy)phenyl]acetonitrile, tert-butyl bis(2-chloroethyl)carbamate, sodium hydride and potassium iodide similarly to the procedure used for intermediate 56. LRMS APCI+ m/z 414 [MH]+ and m/z 245 [SMH]+.

Sources & evidence

ORD record: ord-99a15bfc9377498b88ae6c26e02a8a5c
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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