Propylamine → 6-hydroxy-2,5,7,8-tetramethyl-N-propylchroman-2-carboxamide

HRID 1755537Notes

Reaction equation

[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:31]([NH2:34])[CH2:32][CH3:33]>>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([NH:34][CH2:31][CH2:32][CH3:33])=[O:16])[CH2:6][CH2:5]2

Participants

Reactant 3

HCID 7852Propylamine

HCID 40634Trolox

HCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 672629696-hydroxy-2,5,7,8-tetramethyl-N-propylchroman-2-carboxamideYield 63.3%

Procedure

Following the amide coupling procedure described in protocol A, 502.3 mg 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (2.01 mmol), 358 mg CDI (2.21 mmol) and 130 mg propylamine (2.20 mmol) produced 371 mg of 6-hydroxy-2,5,7,8-tetramethyl-N-propylchroman-2-carboxamide as an off white syrup.

Sources & evidence

ORD record: ord-e3a82684d8d147dbb1b69ed9031de43d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169196B2

Reaction notes

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