3-Thiophenecarboxaldehyde → HCID 63248157, compound

HRID 1711134Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[S:15]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16]1>>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][CH2:20][C:17]2[CH:18]=[CH:19][S:15][CH:16]=2)[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

Reactant 2

HCID 681353-Thiophenecarboxaldehyde

HCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 63248157HCID 63248157, compoundYield 71%

Procedure

Using general procedure A, 4-amino-1-Boc-piperidine (481 mg, 2.40 mmol) and 3-thiophenecarboxaldehyde (228 mg, 2.03 mmol) gave 4-[(thiophen-3-ylmethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil (425 mg, 1.43 mmol, 71%). 1H NMR (CDCl3) δ 1.22-1.36 (m, 3H), 1.45 (s, 9H), 1.80-1.90 (m, 2H), 2.67 (tt, 1H, J=10.1, 3.9 Hz), 2.74-2.86 (m, 2H), 3.85 (s, 2H), 3.95-4.10 (m, 2H), 7.04 (dd, 1H, J=4.8, 1.5 Hz), 7.11-7.14 (m, 1H), 7.29 (dd, 1H, J=5.0, 2.9 Hz).

Sources & evidence

ORD record: ord-8cbb40f26799450ab629df46a2fb03c4
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790747B2

Reaction notes

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