4-[4-(1,4,7-Trioxaoct-1-yl)phenyl]butylamine → 4-[4-(1,4,7,10,13-Pentoxatetradec-1-yl)phenyl]butylamine

HRID 25139Notes

Reaction equation

HRID 25139 reaction equation
O(C1C=CC(CCCCN)=CC=1)CCOCCOC.[O:20]([C:34]1[CH:39]=[CH:38][C:37]([CH:40](C(OCC2C=CC=CC=2)=O)[CH2:41][CH2:42][CH2:43][NH2:44])=[CH:36][CH:35]=1)[CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]>>[O:20]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42][CH2:43][NH2:44])=[CH:36][CH:35]=1)[CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]

Participants

3

Reactant 2

HCID 225661364-[4-(1,4,7-Trioxaoct-1-yl)phenyl]butylamineHCID 673658744-[4-(1,4,7,10,13-Pentoxatetradec-1-yl)phenyl]-N-benzyloxycarbonylbutylamine

Product 1

HCID 225661704-[4-(1,4,7,10,13-Pentoxatetradec-1-yl)phenyl]butylamineYield 95.9%

Procedure

This compound was prepared in a similar fashion to the synthesis of amine 107 from compound 110 (385 mg, 0.78 mmol) to give 266 mg (95%) of compound 111. 1H NMR (300 MHz, CDCl3) δ 1.41-1.54 (m, 2H), 1.60 (br. s, 2H), 2.56 (t, J=7.5 Hz, 2H), 2.70 (t, J=7.0 Hz, 2H), 3.37 (s, 3H), 3.51-3.58 (m, 2H), 3.60-3.77 (m, 10H), 3.84 (m, 2H), 4.10 (t, 5.5 Hz, 2H), 6.83 (d, J=8.3 Hz, 2H), 7.07 (d, J=8.7 Hz, 2H).

Sources & evidence

ORD record
ord-c09ff38e59f248b098c49b5df7121a72
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

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