Cyclopropanecarboxaldehyde → HCID 59837361, compound

HRID 272980Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:29]1([CH:32]=O)[CH2:31][CH2:30]1>>[CH:29]1([CH2:32][N:26]2[CH2:25][CH2:24][N:23]([CH2:22][C:16]3([C:13]4[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)=[CH:11][CH:12]=4)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[CH2:28][CH2:27]2)[CH2:31][CH2:30]1

Participants

Reactant 2

HCID 123114Cyclopropanecarboxaldehyde

HCID 59837542HCID 59837542, compound

Product 1

HCID 59837361HCID 59837361, compoundYield 14%

Procedure

The title compound (26 mg, 14%) was prepared from 1-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}piperazine and cyclopropane carboxaldehyde similarly to the procedure used for example 54. 1H NMR (400 MHz, CDCl3) δ 0.02 (q, 2H), 0.43 (q, 2H), 0.76 (m, 1H), 1.74-1.76 (m, 4H), 1.83-1.89 (m, 2H), 1.95-1.99 (m, 2H), 2.03-2.06 (m, 3H), 2.13 (d, 2H), 2.19-2.21 (m, 4H), 2.26-2.40 (m, 5H), 2.47-2.51 (m, 4H), 2.59 (t, 2H), 3.49 (t, 2H), 3.68-3.72 (m, 2H), 3.98 (t, 2H), 6.82 (d, 2H), 7.17 (d, 2H). HRMS ESI+ m/z 442.3412 [MH]+.

Sources & evidence

ORD record: ord-1bdd067690aa447b89746a4587116d37
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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