Aluminium lithium hydride → HCID 59837371, compound

HRID 273054Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].N1(CC2(C3C=CC(OCCCN4CCOCC4)=CC=3)CCOCC2)CCOCC1>>[CH3:1][NH:2][CH2:3][C:5]1([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:15][CH:16]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

Reactant 3

HCID 21226445Aluminium lithium hydride

HCID 59837355HCID 59837355, compound

HCID 59837484HCID 59837484, compound

Product 1

HCID 59837371HCID 59837371, compoundYield 77%

Procedure

The title compound (252 mg, 77%) was prepared from N-methyl-4-[4-(3-morpholin-4-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carboxamide and a solution of LiAlH4 (10M solution in Et2O) similarly to the procedure used for 4-(3-{4-[4-(morpholin-4-ylmethyl)tetrahydro-2H-pyran-4-yl]phenoxy}propyl)morpholine. 1H NMR (400 MHz, CD3OD) δ 1.85-2.00 (m, 6H), 2.12 (m, 2H), 2.24 (s, 3H), 2.45 (m, 4H), 2.53 (t, 2H), 2.63 (s, 2H), 3.57 (m, 2H), 3.70-3.80 (m, 6H), 4.01 (t, 1H), 6.88 (d, 2H), 7.20 (d, 2H). HRMS ESI+ m/z 349.2477 [MH]+.

Sources & evidence

ORD record: ord-1377bbce212c4ec78f759ec3e3375640
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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