tert-Butyl N-(2-bromoethyl)carbamate → HCID 66818918, compound

HRID 1024800Notes

Reaction equation

HRID 1024800 reaction equation
[C:1]([C:3]1[CH:33]=[CH:32][C:6]([O:7][C:8]2[CH:9]=[C:10]([NH:23][C:24]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[O:25])[CH:11]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=3)[CH:13]=2)=[CH:5][CH:4]=1)#[N:2].[C:34]([O:38][C:39](=[O:44])[NH:40][CH2:41][CH2:42]Br)([CH3:37])([CH3:36])[CH3:35]>>[C:34]([O:38][C:39](=[O:44])[NH:40][CH2:41][CH2:42][N:29]1[CH2:28][CH2:27][CH:26]([C:24](=[O:25])[NH:23][C:10]2[CH:11]=[C:12]([O:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[CH:19][CH:20]=3)[CH:13]=[C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:33][CH:32]=3)[CH:9]=2)[CH2:31][CH2:30]1)([CH3:37])([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 66818471HCID 66818471, compound

Product 1

HCID 66818918HCID 66818918, compoundYield 37.8%

Procedure

Following the procedure of Example 11(e) 4-[3,5-bis-(4-cyano-phenoxy)-phenyl-carbamoyl]-piperidine (0.8 g, 1.82 mmol) and (2-bromo-ethyl)-carbamic acid tert-butyl ester (0.49 g, 2.19 mmol) were used to afford 0.4 g of the required product. 1H NMR (DMSO-d6): δ 1.4 (9H, s), 1.42 (4H, m), 2.31 (3H, m), 1.8 (2H, t), 2.81 (2H, m), 3.15 (1H, m), 3.7 (1H, m), 6.76 (1H, s), 7.26 (6H, m), 7.86 (4H, d).

Sources & evidence

ORD record
ord-78c154cf3b13453890674d39d4e72fbd
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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