1,3-Benzodioxole-5-carboxylic acid → HCID 22633904, compound

HRID 2378358Notes

Reaction equation

HRID 2378358 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]>>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)=[O:12]

Participants

3

Reactant 2

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 258684-Amino-1-butanol

Product 1

HCID 22633904HCID 22633904, compoundYield 75%

Procedure

1,3-Benzodioxole -5-carboxylic acid (2.0 g, 12.0 mmol) and 4-amino-1-butanol (1.4 ml, 15.6 mmol) were coupled according to the procedure of Example 17 to 2.1 g (75% yield) of a pale yellow solid. MP 95-98° C.; 1H NMR (DMSO-d6): δ 1.38-1.65 (m, CH2, CH2), 3.31 (q, CH2), 3.39 (q, CH2), 4.39 (t, NH), 6.08 (s, CH2), 6.98 (d, 1 Ar H), 7.37 (d, 1 Ar H), 7.4 (d-d, 1 Ar H), 8.27 (t, NH) Electrospray Mass Spec: m/z 238.2 (M+H)+.

Sources & evidence

ORD record
ord-4d75ba5411df483bb93d123283e5bd67
Source dataset
uspto-grants-2008_12
Patent number
US07470794B2

Reaction notes

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