4-(Bromomethyl)benzonitrile → HCID 66818661, compound

HRID 1024768Notes

Reaction equation

HRID 1024768 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=2[OH:24])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1>>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:28][C:29]3[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=3)=[CH:19][C:18]=2[O:24][CH2:28][C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 66818673HCID 66818673, compound

Product 1

HCID 66818661HCID 66818661, compoundYield 70.5%

Procedure

{2-[1-(2,4-Dihydroxy benzoyl)piperidin-4-yl]ethyl}carbamic acid tert-butyl ester (1.13 g, 3.1 mmol) and 4-bromomethyl-benzonitrile (2.43 g, 12.4 mmol) and other reagents as described in Example 75(a) were used to afford 1.3 g of the required product. 1H NMR (DMSO-d6): δ 1.35 (8H, s), 2.1 (4H, s), 2.9 (3H, m), 4.55 (4H, d), 5.25 (3H, s), 5.5 (2H, t), 6.8 (1H, m), 7.3 (1H, d), 7.4 (1H, d), 7.5 (4H, d), 7.66 (1H, d), 7.8 (3H, m), 7.86 (2H, m).

Sources & evidence

ORD record
ord-cbd41c737ede44e68f35daa56d5615ee
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

Loading…